Name: 4441-56-9|Cyclohexylboronic acid|98%
Brand: Ambeed
SKU: A214406
Rating: 96 (30 reviews)

1
[ 1009639-59-1 ]
[ 4441-56-9 ]
C₂₃H₃₁N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate In 1,4-dioxane at 90℃; for 16h;	11.A Example 11:; Part A:; To a solution of compound 46 (0.013 mmol) in dioxane (2 ml_) is added cyclohexylboronic acid (2 equivalents), potassium phosphate (0.04 mmol) and dichloro[1 ,1 '-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane (20 mol%). The reaction mixture is de-gassed, flushed with argon and heated at 900C for 16 hours. The precipitates are removed by passing through a plug of celite, washed through with ethyl acetate and the filtrate concentrated. Purification by preparative LC affords compound 80.

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2008/27466, 2008, A1 Location in patent: Page/Page column 64-65

2
[ 4441-56-9 ]
[ 586-78-7 ]
[ 5458-48-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate In 1,2-dimethoxyethane; water at 80℃; for 15h;

Reference： [1]Current Patent Assignee: ALBERT-LUDWIGS-UNIVERSITÄT FREIBURG - WO2004/13068, 2004, A1 Location in patent: Page/Page column 25-26; 28

3
[ 4441-56-9 ]
[ 504-63-2 ]
[ 30169-75-6 ]

Yield	Reaction Conditions	Operation in experiment
72%	With magnesium sulfate In diethyl ether at 20℃; for 18h;
	In hexane byproducts: water; water azeotrope was distilled from a hexane soln. of the boronic acid and HO(CH2)3OH, water was collected in a Dean-Stark trap; the ester was distilled under reduced pressure;

Reference： [1]Fasano, Valerio; McFord, Aidan W.; Butts, Craig P.; Collins, Beatrice S. L.; Fey, Natalie; Alder, Roger W.; Aggarwal, Varinder K. [Angewandte Chemie - International Edition, 2020, vol. 59, # 50, p. 22403 - 22407][Angew. Chem., 2020, vol. 132, # 50, p. 22589 - 22593]
[2]Matteson, Donald S.; Majumdar, Debesh [Organometallics, 1983, vol. 2, p. 230 - 236]

4
[ 4441-56-9 ]
potassium cyclohex-1-ene-1-yl-trifluoroborate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With potassium hydrogen difluoride In diethyl ether; water at 20℃;	XXVI To 1 g 1-cyclohexylboronic acid in 20 ml of diethylether is added 1.86 g potassiumhydrogenefluoride and 0.86 ml water. Then the mixture is stirred over might at ambient temperature. The reaction is evaporated in vacuum and the residue is stirred with diethylether precipitate is filtered and dried under vacuum. Yield: 2.3 g (97% of theory) Mass spectrometry (El): m/z = 130 [M+]

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - WO2009/109549, 2009, A1 Location in patent: Page/Page column 134

5
[ 4441-56-9 ]
[ 106-51-4 ]
[ 3116-98-1 ]

Yield	Reaction Conditions	Operation in experiment
63%	With palladium trifluoroacetate In acetone at 40℃; for 48h; Sonication;
46%	With dipotassium peroxodisulfate; silver nitrate In dichloromethane; water at 23℃; for 4.5h;
45%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer In dichloromethane; water at 20℃; for 10h;	General Procedure for the Reaction of Benzoquinone with Boronic Acid General procedure: To a solution of benzoquinone (0.5 mmol, 1.0 equiv) and [Cp*RhCl2]2 (0.025 mmol, 5 mol%) in CH2Cl2 (2 mL) was added the boronic acid (0.75 mmol, 1.5 equiv), H2O (1 mL). Then the solution was stirred vigorously at r.t. for 10 h. Upon completion, the reaction was diluted with CH2Cl2 (3 mL) and washed with 5% NaHCO3. The layers were separated, and the aqueous layer was extracted with CH2Cl2 (3 × 4 mL), dried over Na2SO4, and was evaporated to give the residue. The residue was then purified by column chromatography on silica gel (EtOAc-PE, 1:10) to provide the corresponding product.

31%	With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] In dichloromethane; water at 20℃; for 12h;	2. General procedure for thereaction of benzoquinone with phenylboronic acid. General procedure: To a solution of benzoquinone (0.5 mmol, 1.0 equiv.) and [Cp*IrCl2]2 (0.025mmol, 5%) in dichloromethane (2 mL) was added the phenylboronic acid (0.75 mmol, 1.5 equiv.) and water (2 mL) Then the solution was stirred vigorously at room temperature for 12 h. Upon completion, the reaction was diluted with dichloromethane (5 mL) and washed with 5% sodium bicarbonate. The layers were separated, and the aqueous layer was extracted with dichloromethane (10 X 3 mL), dried over sodium sulfate, and was evaporated to give the residue. The residue was then purified by column chromatography on silica gel (ethyl acetate / petroleumether = 1:10) to provide the corresponding product.
	With dipotassium peroxodisulfate; silver nitrate In dichloromethane; water at 20℃;

Reference： [1]Walker, Sarah E.; Jordan-Hore, James A.; Johnson, David G.; MacGregor, Stuart A.; Lee, Ai-Lan [Angewandte Chemie - International Edition, 2014, vol. 53, # 50, p. 13876 - 13879][Angew. Chem., 2014, vol. 126, # 50, p. 14096 - 14099,9]
[2]Fujiwara, Yuta; Domingo, Victoriano; Seiple, Ian B.; Gianatassio, Ryan; Del Bel, Matthew; Baran, Phil S. [Journal of the American Chemical Society, 2011, vol. 133, # 10, p. 3292 - 3295]
[3]Wang, Dawei; Ge, Bingyang; Du, Liyong; Miao, Hongyan; Ding, Yuqiang [Synlett, 2014, vol. 25, # 20, p. 2895 - 2898]
[4]Wang, Dawei; Ge, Bingyang; Ju, Anqi; Zhou, Yucheng; Xu, Chongying; Ding, Yuqiang [Journal of Organometallic Chemistry, 2015, vol. 780, p. 30 - 33]
[5]Zheng, Haifeng; Xu, Chaoran; Wang, Yan; Kang, Tengfei; Liu, Xiaohua; Lin, Lili; Feng, Xiaoming [Chemical Communications, 2017, vol. 53, # 49, p. 6585 - 6588]

6
[ 4441-56-9 ]
[ 446065-11-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydrogen difluoride; In methanol; water; at 20℃; for 0.5h;	General procedure: To a solution of boronic acid or pinacol ester (40 mmol) in methanol (100 mL) was added aqueous potassium hydrogen fluoride (50 mL, 4.5 M, 225 mmol). The resulting white slurry was stirred at room temperature for 30 min, concentrated in vacuo and dissolved in hot acetone. The mixture was filtered, the filtrate was concentrated in vacuo and the residue recrystallised from a minimal amount of ether, to afford the corresponding potassium trifluoroborate salt.

Reference： [1]Tetrahedron,2011,vol. 67,p. 8615 - 8621

7
[ 7732-18-5 ]
[ 446065-11-8 ]
[ 4441-56-9 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 7431 - 7441

8
[ 446065-11-8 ]
[ 4441-56-9 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 7431 - 7441

9
[ 4441-56-9 ]
[ 108-93-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	With [bis(acetoxy)iodo]benzene; water; triethylamine In acetonitrile at 20℃; for 0.166667h;	General procedure for syntheses of aromatic alcohols General procedure: To a stirred solution of appropriate organoboronic acids (0.5 mmol, 1.0 equiv.) and Et3N(1.0 mmol, 2.0 equiv.) in CH3CN(acetonitrile: 3 mL, H2O: 11µL, 0.6mmol, 1.2 equiv.), DAIB (0.75 mmol, 1.5 equiv.), dissolved in acetonitrile (2mL) was added drop wise at room temperature and the mixture was allowed to stir for 10 minutes at that temperature. After completion of the reaction indicated by TLC, the reaction mixture was washed with distilled water (3×7 mL) and extracted with CH2Cl2(3×10 mL). The combined organic phase was dried over Na2SO4 and after evaporating the solvent, the residue was purified by column chromatography over silica gel using hexane/EtOAc as eluent to provide the pure target product.
91%	With Fe₂O₃-SiO₂ nanoparticles; air In water at 50℃; for 3h; Green chemistry;	General procedure: In a round bottomed flask 1 mmol phenyl boronic acid, and4mg of Fe2O3SiO2 in 4 ml of the H2O were taken and stirred atroom temperature for appropriate time. Progress of the reactionwas monitored by TLC. After completion of the reaction mixturewas extracted with Ethyl acetate. Further, the organic layer wasseparated and dried with sodium sulfate. The mixture was concentratedin rotary evaporator and product was purified by column chromatography. The product was analyzed by taking 1H and 13CNMR spectroscopy.
91%	With dihydrogen peroxide at 30℃; for 5h; Green chemistry;	General procedure for the oxidation of boronic acids General procedure: A mixture of boronic acid (1mmol), DMC (1.0mL) was taken in 25mL round bottom flask with magnetic stirring bar. Then the reaction was activated by addition of 30% H2O2 (2.0equiv.) and stirred at room temperature for 5h. The progress of reaction was monitored by TLC. After disappearance of starting material, added H2O (1.0mL) in to the reaction mixture. The reaction mixture was then further diluted with ethyl acetate (30mL) and subsequently washed with distilled water (5.0mL). The resulting organic extract was dried over anhydrous sodium sulphate. The solvent was removed under vacuum to get crude product which was purified (if necessary) by column chromatography using silica gel with pet ether and ethyl acetate as solvent system to obtain the pure product. The structure of the product was confirmed by GC-MS, M.P. and 1H NMR spectroscopic techniques.

90%	With sodium chlorite In water at 20℃; for 0.5h;
90%	With dihydrogen peroxide In ethanol at 20℃; for 0.166667h;
88%	With ozone In ethanol; water at 20 - 30℃; for 0.5h;
88%	With pyrene-1,6-dione; oxygen; isopropyl alcohol at 20℃; for 40h; Irradiation; Green chemistry;
87%	With urea hydrogen peroxide adduct In methanol at 27 - 29℃; for 3h; Green chemistry; chemoselective reaction;	2.1 Solution phase protocol: General procedure: To a stirred solution of aryl/alkyl boronic acid (1 mmol) in methanol or acetonitrile solvent (1 ml) was added 1 equiv. of Urea-Hydrogen peroxide (UHP) (2.5 equiv for alkyl boronic acids) at room temperature and the progress of the reaction was monitored by TLC. After completion, the reaction mixture was diluted with water and extracted with dichloromethane (DCM). The combined organic layer was dried over anhydrous sodium sulfate (Na2SO4), evaporated and subjected to silica gel column chromatography for further purification.
86%	With copper(ll) sulfate pentahydrate; ellagic acid In methanol at 60℃; for 8h; Green chemistry;	In situ synthesis of Cu NPs-EA composite: General procedure: In a typical reaction, 10 mol% CuSO4·5H2O, (0.049 g, 0.2 mmol)and 6.7 mol% EA (20 mg) were mixed in methanol followed by2 mmol of phenylboronic acid. This reaction mixture was kept ina preheated oil bath by maintaining the temperature at 60 °C andstirred under atmospheric pressure. After completion of the reac-tion, modified by TLC, the mixture was washed twice with hot ethylacetate to remove the reactant and product. The hot ethyl acetatewas removed from the reaction mixture and the resulting crudeproduct was purified by a column chromatography using silicagel 260 mesh (pet ether:ethyl acetate) ratio (25:75). The recov-ered catalyst was reused for the next run. All the products werecharacterized by1H and13C NMR spectra.
86%	With LACTIC ACID; dihydrogen peroxide In water at 20℃; for 0.5h; Green chemistry;
80%	With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 20℃; for 29h; Irradiation; Green chemistry;
65%	With sodium periodate; iodobenzene In water; acetonitrile at 80℃; for 8h;	General procedure for syntheses of aliphaticalcohols General procedure: Toa stirred solution of appropriate organoboronic acids (2.0 mmol, 1.0 equiv.) and NaIO4 (4.0 mmol, 2.0 equiv.) in CH3CN-H2O(acetonitrile: 6 mL, H2O: 2 mL), iodobenzene (0.2 mmol, 10 mol%) was added and the mixture was heated at 80 0C for 8 h. After thecompletion of reaction, the reaction mixture was cooled and concentrated to a smaller volume and the crude mixture was directly purified by column chromatography over silica gelusing pentane/Et2O as eluent.
61%	With tetrabutylammonium tetrafluoroborate; oxygen In N,N-dimethyl-formamide for 16h; Electrochemical reaction;
60%	With water; 3-chloro-benzenecarboperoxoic acid In ethanol at 20℃; for 6h;
42%	With 2,2-dimethoxy-2-phenylacetophenone; N-ethyl-N,N-diisopropylamine In water at 20℃; for 72h; Irradiation; Green chemistry;	General Procedure for the PhotoOrganocatalytic Hydroxylation of ArylboronicAcids General procedure: Substituted boronic acid (0.60 mmol) was placed in a glass vial and dissolved in water(1.0 mL), followed by 2,2-dimethoxy-2-phenylacetophenone (30.0 mg, 0.12 mmol).DIPEA (580 mg, 4.50 mmol) was added consecutively. The reaction mixture was leftopen stirring at room temperature under household bulb irradiation (2 x 80W householdlamps, see photos below) under open air (in the present of O2) for 72 hours. The reactionmixture was quenched by aqueous solution of HCl (1N, 20 ml). The reaction mixturewas extracted with Et2O (20 mL). The organic layer was washed with brine (20 mL)and dried over Na2SO4. After removal of the solvent in vacuum, the crude product waspurified using flash column chromatography (10% EtOAc in Pet. Ether) to afford thedesired product.
38%	With 1,3-dimethyl-5-ethyl-4a-hydroperoxyalloxazine; oxygen; hydrazine hydrate In methanol; 2,2,2-trifluoroethanol at 20℃; for 2h;
35%	With ammonium hydroxide; potassium nitrate In water at 20℃; for 4h; Electrochemical reaction; chemoselective reaction;
65 %Spectr.	With oxygen; N-ethyl-N,N-diisopropylamine In acetone at 25℃; for 7h; Irradiation;
> 99 %Spectr.	With oxygen; triethylamine In acetonitrile for 4h; Irradiation;	2.3. Photocatalytic hydroxylation of phenylboronic acid General procedure: The photocatalytic hydroxylation of phenylboronic acid wascarried out as following: Catalyst (10 mg) and phenylboronicacid (0.5 mmol) was poured into the mixture solution with triethylamine (TEA, 1.5 mmol) dissolved in the acetonitrile (3 mL).Then, the mixture was transferred into a 10 mL Pyrex glass bottlefilled with pure oxygen at atmospheric pressure. The suspensionswere irradiated by a blue LED lamp. After the reaction, the mixturewas centrifuged to completely remove the catalyst particles. Thefiltered solution was analyzed by 1H NMR spectrum using 1, 3, 5-Trimethoxybenzene as the internal standard.

Reference： [1]Chatterjee, Nachiketa; Chowdhury, Hrishikesh; Sneh, Kumar; Goswami, Avijit [Tetrahedron Letters, 2014, vol. 56, # 1, p. 172 - 174]
[2]Saikia, Indranirekha; Hazarika, Moushumi; Hussian, Najrul; Das, Manash R.; Tamuly, Chandan [Tetrahedron Letters, 2017, vol. 58, # 45, p. 4255 - 4259]
[3]Wagh, Ravindra B.; Nagarkar, Jayashree M. [Tetrahedron Letters, 2017, vol. 58, # 48, p. 4572 - 4575]
[4]Gogoi, Pranjal; Bezboruah, Pranjal; Gogoi, Junali; Boruah, Romesh C. [European Journal of Organic Chemistry, 2013, # 32, p. 7291 - 7294]
[5]Latha, Ganesapandian; Devarajan, Nainamalai; Karthik, Murugan; Suresh, Palaniswamy [Catalysis Communications, 2020, vol. 136]
[6]Bommegowda, Yadaganahalli K.; Mallesha, Ningegowda; Vinayaka, Ajjampura C.; Sadashiva, Maralinganadoddi P. [Chemistry Letters, 2016, vol. 45, # 3, p. 268 - 270]
[7]Zhang, Yuannian; Yang, Xin; Tang, Haidi; Liang, Dong; Wu, Jie; Huang, Dejian [Green Chemistry, 2020, vol. 22, # 1, p. 22 - 27]
[8]Gupta, Surabhi; Chaudhary, Priyanka; Srivastava, Vandana; Kandasamy, Jeyakumar [Tetrahedron Letters, 2016, vol. 57, # 23, p. 2506 - 2510]
[9]Affrose, Abdullah; Azath, Ismail Abulkalam; Dhakshinamoorthy, Amarajothi; Pitchumani, Kasi [Journal of Molecular Catalysis A: Chemical, 2014, vol. 395, p. 500 - 505]
[10]Gupta, Surabhi; Chaudhary, Priyanka; Seva, Lavudi; Sabiah, Shahulhameed; Kandasamy, Jeyakumar [RSC Advances, 2015, vol. 5, # 108, p. 89133 - 89138]
[11]Chen, Yang; Ding, Aishun; Hu, Jianhua [RSC Advances, 2020, vol. 10, # 13, p. 7927 - 7932]
[12]Chatterjee, Nachiketa; Goswami, Avijit [Tetrahedron Letters, 2015, vol. 56, # 12, p. 1524 - 1527]
[13]Jiang, Hao; Lykke, Lennart; Uttrup Pedersen, Steen; Xiao, Wen-Jing; Anker Jorgensen, Karl [Chemical Communications, 2012, vol. 48, # 57, p. 7203 - 7205]
[14]Chen, Dong-Song; Huang, Jing-Mei [Synlett, 2013, vol. 24, # 4, p. 499 - 501]
[15]Sideri, Ioanna K.; Voutyritsa, Errika; Kokotos, Christoforos G. [Synlett, 2018, vol. 29, # 10, p. 1324 - 1328]
[16]Kotoucova, Hana; Strnadova, Iveta; Kovandova, Martina; Chudoba, Josef; Dvorakova, Hana; Cibulka, Radek [Organic and Biomolecular Chemistry, 2014, vol. 12, # 13, p. 2137 - 2142]
[17]Qi, Hong-Lin; Chen, Dong-Song; Ye, Jian-Shan; Huang, Jing-Mei [Journal of Organic Chemistry, 2013, vol. 78, # 15, p. 7482 - 7487]
[18]Simlandy, Amit Kumar; Bhattacharyya, Biswajit; Pandey, Anshu; Mukherjee, Santanu [ACS Catalysis, 2018, vol. 8, # 6, p. 5206 - 5211]
[19]Anpo, Masakazu; Cheng, Jiajia; Huang, Caijin; Ou, Honghui; Ren, Wei; Wang, Xinchen [Journal of Catalysis, 2020, vol. 389, p. 636 - 645]

10
[ 76-09-5 ]
[ 4441-56-9 ]
[ 87100-15-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With magnesium sulfate; In diethyl ether; at 20℃; for 16h;Inert atmosphere; Schlenk technique;	General procedure: A mixture of boronic acid (1.0 equiv), pinacol (1.0 equiv) and anhydrous MgSO4 (4.0 equiv) in Et2O (0.5 M) was stirred at r.t. for 16 h. The reaction mixture was filtered and the solvent removed in vacuo. The crude material was purified by distillation or flash column chromatography to give the pure boronic ester.
14.8 g	In diethyl ether; at 0℃; for 72h;Inert atmosphere;	Magnesium chippings (3.8 g, 156 mmol, 1.0 eq.) were added to a dried flaskunder argon atmosphere and suspended with dry Et2O (20 mL). A small amount(10 mL) of a solution of cyclohexyl bromide (19.2 mL, 156 mmol, 1.0 eq.) in dryEt2O (200 mL) was added to the magnesium and the activation of the Grignardformation was accelerated by addition of an iodine crystal and heating.Afterwards, the rest of the solution of cyclohexyl bromide in (19.2 mL, 156 mmol, 1.0 eq.) in Et2O(200 mL) was added dropwise over 2 h. The reaction mixture was heated to reflux for 1 h and thenstirred for 17 h.[a] The reaction mixture was transferred via decantation under a constant flow of argoninto a well dried addition funnel and added dropwise to a solution of trimethyl borate (17.7 mL, 159mmol, 1.02 eq) in Et2O (450 mL) at -78 C for 2 h. The reaction mixture was then quenched bydropwise addition of HCl (10 wt.%, 200 mL) and extracted with Et2O (2 x 100 mL), dried over MgSO4and the solvent was removed in vacuo to give c-hex-B(OH)2 as a white solid (Crude: 15.96 g, 125mmol, 80%). The solid residue was used without further purification and dissolved in dry Et2O(150 mL). Pinacol (17.9 g, 151 mmol, 1.2 eq.) was added in portions at 0 C and then the reactionmixture was stirred for 72 h.[b] As a desiccant MgSO4 (5 g) was added to the reaction mixture andstirring was continued for 48 h.[*c] Then the residue was filtered over celite and washed with Et2O (2 x25 mL) and the solvent was removed in vacuo to give a colorless oil. The residue was purified bydistillation (b.p. 65-80 C, at 4.7-5.0 mbar). The product, c-hex-B(pin) (6) was obtained as a colorlessoil (14.8 g, 70.4 mmol, 56%).

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 6549 - 6553
Angew. Chem.,2019,vol. 131,p. 6621 - 6625,5
[2]Journal of the American Chemical Society,2012,vol. 134,p. 11298 - 11298
[3]Synthesis,2016,vol. 48,p. 3241 - 3253
[4]Journal of the American Chemical Society,2018,vol. 140,p. 14677 - 14686
[5]Journal of the American Chemical Society,2017,vol. 139,p. 9519 - 9522
[6]Synlett,2018,vol. 29,p. 1092 - 1094

11
[ 45842-10-2 ]
[ 4441-56-9 ]
[ 54051-40-0 ]

Yield	Reaction Conditions	Operation in experiment
54%	With manganese(III) tris(acetylacetonate) In toluene at 80℃; for 23h; Inert atmosphere;
	With C₆H₄NCH₂CHCCH₂; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-κN1,κN1′]bis[3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC]iridium hexafluorophosphate; oxygen; trifluoroacetic acid In 1,2-dichloro-ethane at 20℃; for 24h; Sealed tube; Irradiation;
	With 1,10-Phenanthroline; copper(II) bis(trifluoromethanesulfonate); aniline; anhydrous silver carbonate In tetrahydrofuran at 60℃; for 24h;

With potassium peroxodisulfate; tris(2,2′-bipyridine)ruthenium(II) dichloride hexahydrate; N-methacryloyl-N-methylbenzamide In water monomer; 1,2-dichloro-ethane at 20℃; for 36h; Inert atmosphere; Schlenk technique; Irradiation;

6. Control experiments A 25 mL Schlenk tube was equipped with a stirring bar, acryloylbenzamide 1 (0.5 mmol), alkylboronic acid 2 (1.5 mmol, 3 equiv.), K2S2O8(1 mol, 2 equiv.), TEMPO (2 mol, 4 equiv.) andRu(bpy)3Cl2·6H2O (0.01 mmol, 2 mol%). The mixture was degassed by using standard Schlenktechniques with an oil pump. The mixed solvent of DCE (5 mL) and H2O (1 mL) were injectedinto the reaction tube. Then, the reaction mixture was placed at a distance of about 2 cm froma 5 W blue LED and stirred at room temperature. After 36 h, the reaction mixture was dilutedwith DCM (30 mL) and H2O (25 mL). The aqueous layer was extracted with DCM (2×30 mL).The combined organic layers were washed with saturated brine (25 mL) dried over Na2SO4.The organic solution was concentrated under reduced pressure. TLC shows that the product 3awas not formed and 1-(cyclohexyloxy)-2,2,6,6-tetramethylpiperidine was detected by GC-MS

Reference： [1]Tobisu, Mamoru; Koh, Keika; Furukawa, Takayuki; Chatani, Naoto [Angewandte Chemie - International Edition, 2012, vol. 51, # 45, p. 11363 - 11366][Angew. Chem., 2012, vol. 124, # 45, p. 11525 - 11528,4]
[2]Dong, Jianyang; Yue, Fuyang; Song, Hongjian; Liu, Yuxiu; Wang, Qingmin [Chemical Communications, 2020, vol. 56, # 83, p. 12652 - 12655]
[3]Gockel, Samuel N.; Lee, SangHyun; Gay, Brittany L.; Hull, Kami L. [ACS Catalysis, 2021, vol. 11, # 9, p. 5166 - 5171]
[4]Fu, Jiahui; Cai, Xingxing; Liu, Yihuo; Li, Jinghua; Cheng, Dongping; Xu, Xiaoliang [Synthesis, 2022, vol. 54, # 11, p. 2707 - 2723]

12
[ 4441-56-9 ]
[ 20681-51-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: toluene / 4 h / Dean-Stark; Inert atmosphere 2: potassium hydroxide / toluene / 4 h / Dean-Stark; Inert atmosphere; Reflux 3: [Ir(dF(CF₃)ppy)2(bpy)](PF₆) / acetone; methanol / 11 h / 20 °C / Inert atmosphere; UV-irradiation

Reference： [1]Yasu, Yusuke; Koike, Takashi; Akita, Munetaka [Advanced Synthesis and Catalysis, 2012, vol. 354, # 18, p. 3414 - 3420]

13
potassium hydrogen difluoride [ No CAS ]
[ 4441-56-9 ]
[ 446065-11-8 ]

Reference： [1]European Journal of Organic Chemistry,2013,p. 4909 - 4917
[2]Organic Letters,2017,vol. 19,p. 2426 - 2429
[3]Organic Letters,2017,vol. 19,p. 3612 - 3615

14
[ 4767-03-7 ]
[ 4441-56-9 ]
C₁₁H₁₉BO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	In tetrahydrofuran; cyclohexane; toluene at 20℃;	2.1 Example 2 1) Add 13.36 g (0.098 mol) of 2,2-dimethylol propionic acid, 12.54 g (0.098 mol) of cyclohexylboronic acid, and 50 mL of tetrahydrofuran to a 250 mL single-mouth bottle to yield a solution. Stir the solution at room temperature for 3 h, add 80 mL of toluene to the solution, heat and reflux the solution for 1 h. Cool the solution to room temperature, add 80 mL of cyclohexane to the solution until a solid substance begins to precipitate. Thereafter, heat the solution again until the solution is refluxed; cool the solution for allowing crystals to precipitate. Separate the crystals from the solution by filtration, and dry the crystals in the vacuum at the temperature between 70 and 75°C to a constant weight. 12.28 g of intermediate II-2 is obtained, and the yield thereof is 75.0%.
75%	In tetrahydrofuran; toluene at 20 - 80℃; for 4h;	2.1 EXAMPLE 2 1) Add 13.36 g (0.098 mol) of 2,2-dimethylol propionic acid, 12.54 g (0.098 mol) of cyclohexylboronic acid, and 50 mL of tetrahydrofuran to a 250 mL single-mouth bottle to yield a solution. Stir the solution at room temperature for 3 h, add 80 mL of toluene to the solution, heat and reflux the solution for 1 h. Cool the solution to room temperature, add 80 mL of cyclohexane to the solution until a solid substance begins to precipitate. Thereafter, heat the solution again until the solution is refluxed; cool the solution for allowing crystals to precipitate. Separate the crystals from the solution by filtration, and dry the crystals in the vacuum at the temperature between 70 and 75° C. to a constant weight. 12.28 g of intermediate II-2 is obtained, and the yield thereof is 75.0%.

Reference： [1]Current Patent Assignee: TIANJIN WEIJIE TECHNOLOGY - EP2662377, 2013, A1 Location in patent: Paragraph 0025
[2]Current Patent Assignee: TIANJIN WEIJIE TECHNOLOGY - US2013/296550, 2013, A1 Location in patent: Paragraph 0032

15
[ 4441-56-9 ]
[ 931-59-9 ]
[ 7570-92-5 ]

Yield	Reaction Conditions	Operation in experiment
65%	With Pd(2-[2-(benzylthio)phenyliminomethyl]-4-bromophenol-(H))Cl; potassium carbonate In N,N-dimethyl-formamide at 90℃; for 5h; Sealed tube; Inert atmosphere;	Sulfides 4; Typical Procedure General procedure: A sealed tube was charged with sulfenyl chloride 2a (219mg, 1 mmol), phenylboronic acid (3a) (135 mg, 1 mmol),K2CO3 (254 mg, 2 mmol), catalyst 1a (2 mol%, 10 mg) andDMF (2 mL). The mixture was stirred at 90 °C under an N2atm for 5 h. After completion of the reaction, the mixturewas cooled to r.t. and extracted with EtOAc (2 × 10 mL). The combined extracts were dried over anhydrous Na2SO4,filtered and the solvent removed under reduced pressure.The crude residue was purified by flash chromatographyover silica gel to provide product 4a (166 mg, 89%).

Reference： [1]Gogoi, Prasanta; Kalita, Mukul; Barman, Pranjit [Synlett, 2014, vol. 25, # 6, p. 866 - 870]

16
[ 4441-56-9 ]
[ 130-15-4 ]
[ 34987-31-0 ]

Yield	Reaction Conditions	Operation in experiment
36%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer In dichloromethane; water at 20℃; for 10h;	General Procedure for the Reaction of Benzoquinone with Boronic Acid General procedure: To a solution of benzoquinone (0.5 mmol, 1.0 equiv) and [Cp*RhCl2]2 (0.025 mmol, 5 mol%) in CH2Cl2 (2 mL) was added the boronic acid (0.75 mmol, 1.5 equiv), H2O (1 mL). Then the solution was stirred vigorously at r.t. for 10 h. Upon completion, the reaction was diluted with CH2Cl2 (3 mL) and washed with 5% NaHCO3. The layers were separated, and the aqueous layer was extracted with CH2Cl2 (3 × 4 mL), dried over Na2SO4, and was evaporated to give the residue. The residue was then purified by column chromatography on silica gel (EtOAc-PE, 1:10) to provide the corresponding product.
34%	With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] In dichloromethane; water at 20℃; for 12h;	2. General procedure for thereaction of benzoquinone with phenylboronic acid. General procedure: To a solution of benzoquinone (0.5 mmol, 1.0 equiv.) and [Cp*IrCl2]2 (0.025mmol, 5%) in dichloromethane (2 mL) was added the phenylboronic acid (0.75 mmol, 1.5 equiv.) and water (2 mL) Then the solution was stirred vigorously at room temperature for 12 h. Upon completion, the reaction was diluted with dichloromethane (5 mL) and washed with 5% sodium bicarbonate. The layers were separated, and the aqueous layer was extracted with dichloromethane (10 X 3 mL), dried over sodium sulfate, and was evaporated to give the residue. The residue was then purified by column chromatography on silica gel (ethyl acetate / petroleumether = 1:10) to provide the corresponding product.

Reference： [1]Wang, Dawei; Ge, Bingyang; Du, Liyong; Miao, Hongyan; Ding, Yuqiang [Synlett, 2014, vol. 25, # 20, p. 2895 - 2898]
[2]Wang, Dawei; Ge, Bingyang; Ju, Anqi; Zhou, Yucheng; Xu, Chongying; Ding, Yuqiang [Journal of Organometallic Chemistry, 2015, vol. 780, p. 30 - 33]

17
[ 51050-54-5 ]
[ 4441-56-9 ]
3-cyclohexyl-1H-isochromen-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; ruphos In water; N,N-dimethyl-formamide at 80℃; for 0.5h; Inert atmosphere; Sealed tube;	Typical procedure for the palladium-catalyzed synthesis of 3-phenyl isochromen-1-one, 3a General procedure: A sealed tube containing PdCl2(PPh3)2 (38.96mg, 0.055mmol, and 5mol%), Ruphos (5mol%) 3-chloroisochromen-1-one 1a (200.45mg, 1.11mmol), arylboronic acid 2a (1.22mmol), and K2CO3 (306.82mg, 2.22mmol) were purged with nitrogen gas three times. Then, DMF (3.00mL) was added with a syringe. The reaction mixture was stirred at 80°C for 30min and was diluted with ethyl acetate (30mL). The mixture was filtered through a Celite bed and washed with ethyl acetate. The filtrate was concentrated under reduced pressure and the residue was purified on a silica gel column using hexane/ethyl acetate as eluent to afford the desired product, 3a.See Supporting document for spectral data of compounds 3a-zb and 4a-c

Reference： [1]Kumar, Yadavalli Suneel; Dasaradhan, Changalaraya; Prabakaran, Kamalakannan; Manivel, Pitchai; Nawaz Khan, Fazlur-Rahman; Jeong, Euh Duck; Chung, Eun Hyuk [Tetrahedron Letters, 2015, vol. 56, # 7, p. 941 - 945]

18
[ 4441-56-9 ]
[ 1950-68-1 ]
[ 59693-94-6 ]

Reference： [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 928 - 932

19
[ 4441-56-9 ]
[ 655-48-1 ]
(±)-(4RS,5RS)-2-cyclohexyl-4,5-diphenyl-1,3,2-dioxaborolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium sulfate In diethyl ether at 20℃; for 25h;	(±)-(4R,5R)-2-Cyclohexyl-4,5-diphenyl-1,3,2-dioxaborolane (13c) A solution of (±)-syn-1,2-diphenyl-ethan-1,2-diol (23, 2.05 g, 9.57 mmol) in Et2O (10 mL) was treated with cyclohexylboronicacid (1.23 g, 9.61 mmol) followed by anhydrous Na2SO4 (1.36 g, 9.58 mmol). The resultingsuspension was stirred at rt for 25 h then filtered and the filter cake was washed with Et2O (3x10mL). The filtrate and combined washings were concentrated in vacuo and the residue was purifiedby column chromatography (SiO2, eluting with 10% EtOAc in hexanes) to afford the racemicboronate (±)-13c (2.79 g, 9.11 mmol, 95%) as a colorless oil: IR (neat) 3063, 3031, 2925, 2848,1948, 1876, 1804, 1604, 1496, 1388, 1107, 1016, 759, 697 cm-1; 1H NMR (400 MHz, CDCl3) δ7.42-7.32 (6H, m), 7.30-7.27 (4H, m), 5.14 (2H, s), 1.90-1.82 (2H, m), 1.75-1.63 (3H, m), 1.58-1.50(2H, m), 1.45-1.25 (4H, m) ppm; 13C NMR (100 MHz, CDCl3) δ 141.0 (2C, 0), 129.0 (4C, 1), 128.4(2C, 1), 125.8 (4C, 1), 86.5 (2C, 1), 28.3 (2C, 2), 27.4 (2C, 2), 27.0 (2), 22.0 (1, broad) ppm. 1H and13C NMR spectral data are in agreement with those previously reported by Whiting et al.S7

Reference： [1]Hoyt, Amanda L.; Blakemore, Paul R. [Tetrahedron Letters, 2015, vol. 56, # 23, p. 2980 - 2982]

20
[ 4441-56-9 ]
[ 527-61-7 ]
[ 129453-22-1 ]

Yield	Reaction Conditions	Operation in experiment
75%	With dipotassium peroxodisulfate; silver nitrate In water at 20℃;

Reference： [1]Yue, Yanni; Novianti, Maria L.; Tessensohn, Malcolm E.; Hirao, Hajime; Webster, Richard D. [Organic and Biomolecular Chemistry, 2015, vol. 13, # 48, p. 11732 - 11739]

21
[ 4441-56-9 ]
[ 13220-57-0 ]
6-cyclohexyl-6-hydroxy-6H-indolo[2,1-b]quinazolin-12-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With bis(acetylacetonate)nickel(II); potassium carbonate In chlorobenzene at 120℃; for 24h; Schlenk technique;	General Procedure for the Ni(acac)2 catalyzed 1,2-addition of alkylboronic acids General procedure: Tryptanthrins (0.2 mmol), alkyl boric acids (1 mmol), Ni(acac)2 (0.03 mmol), potassiumcarbonate (0.4 mmol) and 2 mL chlorobenzene were added to a Schlenk tube. Then theresulting mixture was stirred at 120 oC for specific time until the reaction was completed.The reaction mixture was purified through flash column chromatography on a silica gel(Rf= 0.2-0.3, CH2Cl2; Eluent: Petroleum ether: dichloromethane= 1:20 to puredichloromethane) to yield the targeting products

Reference： [1]Chen, Wei-Long; Liu, Chong-Xing; Xiao, Hong-Ping; Jiang, Jun [Synlett, 2016, vol. 27, # 13, p. 1989 - 1992]

22
[ 4441-56-9 ]
8-fluoroindolo[2,1-b]quinazoline-6,12-dione [ No CAS ]
6-cyclohexyl-8-fluoro-6-hydroxy-6H-indolo[2,1-b]quinazolin-12-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With bis(acetylacetonate)nickel(II); potassium carbonate In chlorobenzene at 120℃; for 40h; Schlenk technique;	General Procedure for the Ni(acac)2 catalyzed 1,2-addition of alkylboronic acids General procedure: Tryptanthrins (0.2 mmol), alkyl boric acids (1 mmol), Ni(acac)2 (0.03 mmol), potassiumcarbonate (0.4 mmol) and 2 mL chlorobenzene were added to a Schlenk tube. Then theresulting mixture was stirred at 120 oC for specific time until the reaction was completed.The reaction mixture was purified through flash column chromatography on a silica gel(Rf= 0.2-0.3, CH2Cl2; Eluent: Petroleum ether: dichloromethane= 1:20 to puredichloromethane) to yield the targeting products

Reference： [1]Chen, Wei-Long; Liu, Chong-Xing; Xiao, Hong-Ping; Jiang, Jun [Synlett, 2016, vol. 27, # 13, p. 1989 - 1992]

23
[ 4441-56-9 ]
Methyltryptanthrine [ No CAS ]
6-cyclohexyl-6-hydroxy-8-methyl-6H-indolo[2,1-b]quinazolin-12-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With bis(acetylacetonate)nickel(II); potassium carbonate In chlorobenzene at 120℃; for 40h; Schlenk technique;	General Procedure for the Ni(acac)2 catalyzed 1,2-addition of alkylboronic acids General procedure: Tryptanthrins (0.2 mmol), alkyl boric acids (1 mmol), Ni(acac)2 (0.03 mmol), potassiumcarbonate (0.4 mmol) and 2 mL chlorobenzene were added to a Schlenk tube. Then theresulting mixture was stirred at 120 oC for specific time until the reaction was completed.The reaction mixture was purified through flash column chromatography on a silica gel(Rf= 0.2-0.3, CH2Cl2; Eluent: Petroleum ether: dichloromethane= 1:20 to puredichloromethane) to yield the targeting products

Reference： [1]Chen, Wei-Long; Liu, Chong-Xing; Xiao, Hong-Ping; Jiang, Jun [Synlett, 2016, vol. 27, # 13, p. 1989 - 1992]

24
[ 4441-56-9 ]
8-methoxyindolo[2,1-b]quinoxazoline-6,12-dione [ No CAS ]
6-cyclohexyl-6-hydroxy-8-methoxy-6H-indolo[2,1-b]quinazolin-12-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With bis(acetylacetonate)nickel(II); potassium carbonate In chlorobenzene at 120℃; for 40h; Schlenk technique;	General Procedure for the Ni(acac)2 catalyzed 1,2-addition of alkylboronic acids General procedure: Tryptanthrins (0.2 mmol), alkyl boric acids (1 mmol), Ni(acac)2 (0.03 mmol), potassiumcarbonate (0.4 mmol) and 2 mL chlorobenzene were added to a Schlenk tube. Then theresulting mixture was stirred at 120 oC for specific time until the reaction was completed.The reaction mixture was purified through flash column chromatography on a silica gel(Rf= 0.2-0.3, CH2Cl2; Eluent: Petroleum ether: dichloromethane= 1:20 to puredichloromethane) to yield the targeting products

Reference： [1]Chen, Wei-Long; Liu, Chong-Xing; Xiao, Hong-Ping; Jiang, Jun [Synlett, 2016, vol. 27, # 13, p. 1989 - 1992]

25
[ 3978-81-2 ]
[ 4441-56-9 ]
4-(tert-butyl)-2-cyclohexylpyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: 4-tert-butylpyridine With trifluoroacetic acid In 1,2-dichloro-ethane at 20℃; for 0.166667h; Green chemistry; Stage #2: cyclohexylboronic acid With oxygen In 1,2-dichloro-ethane at 110℃; for 12h; Green chemistry;
63%	With [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; oxygen; trifluoroacetic acid In 1,2-dichloro-ethane at 20℃; for 24h; Sealed tube; Irradiation;
53%	With tris(2,2'-bipyridyl)ruthenium dichloride; 1-acetoxy-1,2-benziodoxol-3-one at 30℃; for 16h; Inert atmosphere; Irradiation;

Reference： [1]Zhang, Lizhi; Liu, Zhong-Quan [Organic Letters, 2017, vol. 19, # 24, p. 6594 - 6597]
[2]Dong, Jianyang; Yue, Fuyang; Song, Hongjian; Liu, Yuxiu; Wang, Qingmin [Chemical Communications, 2020, vol. 56, # 83, p. 12652 - 12655]
[3]Li, Guo-Xing; Morales-Rivera, Christian A.; Wang, Yaxin; Gao, Fang; He, Gang; Liu, Peng; Chen, Gong [Chemical Science, 2016, vol. 7, # 10, p. 6407 - 6412]

26
[ 3796-24-5 ]
[ 4441-56-9 ]
2,6-dicyclohexyl-4-(trifluoromethyl)pyridine [ No CAS ]

Reference： [1]Chemical Science,2016,vol. 7,p. 6407 - 6412

27
[ 95-16-9 ]
[ 4441-56-9 ]
[ 40115-03-5 ]

Yield	Reaction Conditions	Operation in experiment
88%	With tris(2,2'-bipyridyl)ruthenium dichloride; 1-acetoxy-1,2-benziodoxol-3-one at 30℃; for 2h; Inert atmosphere; Irradiation; regioselective reaction;
70%	Stage #1: 1,3-Benzothiazole With trifluoroacetic acid In 1,2-dichloro-ethane at 20℃; for 0.166667h; Green chemistry; Stage #2: cyclohexylboronic acid With oxygen In 1,2-dichloro-ethane at 110℃; for 12h; Green chemistry;
54%	With [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; oxygen; trifluoroacetic acid In 1,2-dichloro-ethane at 20℃; for 24h; Sealed tube; Irradiation;

Reference： [1]Li, Guo-Xing; Morales-Rivera, Christian A.; Wang, Yaxin; Gao, Fang; He, Gang; Liu, Peng; Chen, Gong [Chemical Science, 2016, vol. 7, # 10, p. 6407 - 6412]
[2]Zhang, Lizhi; Liu, Zhong-Quan [Organic Letters, 2017, vol. 19, # 24, p. 6594 - 6597]
[3]Dong, Jianyang; Yue, Fuyang; Song, Hongjian; Liu, Yuxiu; Wang, Qingmin [Chemical Communications, 2020, vol. 56, # 83, p. 12652 - 12655]

28
[ 4441-56-9 ]
[ 104227-87-4 ]
2-(2-(2-amino-6-cyclohexyl-9H-purin-9-yl)ethyl)propane-1,3-diyl diacetate [ No CAS ]

Reference： [1]Chemical Science,2016,vol. 7,p. 6407 - 6412

29
[ 4441-56-9 ]
[ 119-60-8 ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 1856 - 1863

30
potassium hydrogen bifluoride [ No CAS ]
[ 4441-56-9 ]
[ 446065-11-8 ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 1856 - 1863

31
[ 59171-72-1 ]
[ 4441-56-9 ]
methyl 5-cyclohexyl-2-phenyloxazole-4-carboxylate [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 6084 - 6088

32
[ 91-22-5 ]
[ 4441-56-9 ]
[ 123005-17-4 ]

Yield	Reaction Conditions	Operation in experiment
87%	Stage #1: quinoline With trifluoroacetic acid In 1,2-dichloro-ethane at 20℃; for 0.166667h; Green chemistry; Stage #2: cyclohexylboronic acid With oxygen In 1,2-dichloro-ethane at 110℃; for 12h; Green chemistry;

Reference： [1]Zhang, Lizhi; Liu, Zhong-Quan [Organic Letters, 2017, vol. 19, # 24, p. 6594 - 6597]

33
[ 586-95-8 ]
[ 4441-56-9 ]
(2-cyclohexylpyridin-4-yl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: pyridine-4-methanol With acetic acid; trifluoroacetic acid In acetonitrile at 20℃; for 0.166667h; Green chemistry; Stage #2: cyclohexylboronic acid With oxygen In acetonitrile at 110℃; for 12h; Green chemistry;

Reference： [1]Zhang, Lizhi; Liu, Zhong-Quan [Organic Letters, 2017, vol. 19, # 24, p. 6594 - 6597]

34
[ 1632-83-3 ]
[ 4441-56-9 ]
[ 106380-62-5 ]

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: 1-Methylbenzimidazole With trifluoroacetic acid In 1,2-dichloro-ethane at 20℃; for 0.166667h; Green chemistry; Stage #2: cyclohexylboronic acid With oxygen In 1,2-dichloro-ethane at 110℃; for 12h; Green chemistry; Further stages;

Reference： [1]Zhang, Lizhi; Liu, Zhong-Quan [Organic Letters, 2017, vol. 19, # 24, p. 6594 - 6597]

35
[ 491-36-1 ]
[ 4441-56-9 ]
[ 26059-80-3 ]

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: 4-Hydroxyquinazoline With trifluoroacetic acid In 1,2-dichloro-ethane at 20℃; for 0.166667h; Green chemistry; Stage #2: cyclohexylboronic acid With oxygen In 1,2-dichloro-ethane at 110℃; for 12h; Green chemistry;

Reference： [1]Zhang, Lizhi; Liu, Zhong-Quan [Organic Letters, 2017, vol. 19, # 24, p. 6594 - 6597]

36
[ 1558-17-4 ]
[ 4441-56-9 ]
2-cyclohexyl-4,6-dimethylpyrimidine [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 6594 - 6597

37
[ 4441-56-9 ]
[ 6493-05-6 ]
8-cyclohexyl-3,7-dimethyl-1-(5-oxohexyl)-1H-purine-2,6(3H,7H)-dione [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 6594 - 6597

38
[ 68797-61-5 ]
[ 4441-56-9 ]
[ 285139-92-6 ]

Yield	Reaction Conditions	Operation in experiment
61.2%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 120℃; for 12h;Inert atmosphere;	1) In a 250 ml three-neck flask, weigh out 0.05 mol of <strong>[68797-61-5]5-bromo-4,6-dichloropyrimidine</strong>, 0.06 mol of cyclohexylboronic acid,100ml of toluene is stirred and dissolved, protected by nitrogen,Add 0.0025mol Pd(PPh3)4, 0.1mol potassium carbonate,A 50 ml mixture of water and ethanol in a 1:1 volume ratioStir and warm up to 120C, reflux for 12 hours, sample the plate,No residual <strong>[68797-61-5]5-bromo-4,6-dichloropyrimidine</strong> is shown, the reaction is complete; naturally cooled to room temperature, filtered, the filtrate layered, and the organic phase was removed by rotary evaporation under reduced pressure Fractions were passed over a neutral silica gel column to give Intermediate 1-1,HPLC purity 99.3%, yield 61.2%;

Reference： [1]Patent: CN107880031,2018,A .Location in patent: Paragraph 0055; 0057

39
[ 65739-06-2 ]
[ 4441-56-9 ]
[ 1821-36-9 ]

Yield	Reaction Conditions	Operation in experiment
63%	With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 110℃; for 24h; Molecular sieve; Inert atmosphere; Schlenk technique;	General procedure for the synthesis of amines General procedure: To a mixture of PhN=NNHTs (1 mmol), boronic acid (1.5 mmol) 4 Å MS (0.25 g) and freshly distilled DBU (3 mmol), dry toluene (2 mL) was added in a Schlenk flask under nitrogen atmosphere. The tube was caped tightly and heated at 110 °C for 24 h. After completion of reaction, water was added to the reaction mixture and extracted with EtOAc. The EtOAc layer was separated, washed with brine, dried over Na2SO4, and evaporated. Purification of the crude product by flash chromatography over silica gel (230-400 mesh) with petroleum ether-EtOAc as eluent gave the pure product.

Reference： [1]Sarma, Manas Jyoti; Phukan, Prodeep [Synthetic Communications, 2018, vol. 48, # 6, p. 656 - 662]

40
[ 1279123-63-5 ]
[ 4441-56-9 ]
[ 446065-11-8 ]

Yield	Reaction Conditions	Operation in experiment
79%	In methanol; water; for 2h;Inert atmosphere;	General procedure: To the solution of alkyl boronic acidor pinacol ester (10 mmol) in methanol (20 mL) was added saturated aqueous KHF2(15 mL, 3.91 g, 50 mmol, 5.0 equiv). The resulting suspension was stirred for 2 h andthen concentrated to dryness. The residue, a white solid, was extracted with hotacetone, and the combined filtered extracts were concentrated to approximately 5 mL.Ether (or CH2Cl2) was added and the resultant precipitate was collected and dried toafford the potassium trifluoroborate as a white solid.

Reference： [1]Beilstein Journal of Organic Chemistry,2018,vol. 14,p. 1215 - 1221
[2]Journal of the American Chemical Society,2019,vol. 141,p. 16237 - 16242

41
[ 4441-56-9 ]
[ 91-44-1 ]
3-cyclohexyl-7-(diethylamino)-4-methyl-2H-chromen-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With oxygen; trifluoroacetic acid In acetic acid; acetonitrile at 110℃; for 6h; chemoselective reaction;

Reference： [1]Ling, Anbo; Zhang, Lizhi; Tan, Ren Xiang; Liu, Zhong-Quan [Journal of Organic Chemistry, 2018, vol. 83, # 23, p. 14489 - 14497]

42
[ 4441-56-9 ]
[ 4876-10-2 ]
4-(bromomethyl)-3-cyclohexylquinolin-2(1H)-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 14489 - 14497

43
[ 956833-12-8 ]
[ 4441-56-9 ]
methyl 2-(cyclohexylmethyl)-3-phenylacrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81.33%	With 1,4-diaza-bicyclo[2.2.2]octane; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate In 1-methyl-pyrrolidin-2-one at 20℃; for 24h; Schlenk technique; Inert atmosphere; Irradiation;	1 Example 1 In a Schlenk tube, successively add methyl 2-((tert-butoxycarbonyloxy)(phenyl)methyl)acrylate (146.2 mg, 0.5 mmol), cyclohexylboronic acid (96.0 mg, 0.75 mmol), 1,4-diazabicyclo[2.2.2]octane (11.2 mg, 0.1 mmol), Ir[dF(CF3)ppy]2(dtbbpy)PF6 (5.6 mg, 0.005 mmol) and N-methylpyrrolidone (3 mL) ), under a nitrogen atmosphere, stirred at room temperature for 24 h under a white light irradiation of a 45 W energy-saving lamp. After the reaction was completed, the resulting reaction solution was washed with 0.1 mol/L of dilute hydrochloric acid. The organic layer was washed three times with saturated brine and dried over anhydrous sodium sulfate. After drying the solvent, it was separated by silica gel column chromatography, using PE/EA (20/1) as eluent, and the eluent containing the desired product was collected to give the pale yellow target product methyl 2-(cyclohexylmethyl)-3-phenylacrylate, yield 81.33%.

Reference： [1]Current Patent Assignee: ZHEJIANG UNIVERSITY OF TECHNOLOGY - CN108774129, 2018, A Location in patent: Paragraph 0040-0041; 0043; 0045; 0047; 0049; 0051; 0053

44
[ 87100-15-0 ]
[ 4441-56-9 ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 6554 - 6558
Angew. Chem.,2019,vol. 131,p. 6626 - 6630,5

45
[ 4441-56-9 ]
[ 111875-47-9 ]
4-(cyclohexylmethyl)-2,4-dimethylisoquinoline-1,3(2H,4H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium peroxodisulfate; tris(2,2′-bipyridine)ruthenium(II) dichloride hexahydrate In water monomer; 1,2-dichloro-ethane at 20℃; for 36h; Inert atmosphere; Schlenk technique; Irradiation;	Alkylated Isoquinoline-1,3(2H,4H)-diones 3; General Procedure General procedure: A 25-mL Schlenk tube was equipped with a stirring bar, acryloylbenzamide1 (0.5 mmol), alkylboronic acid 2 (1.5 mmol, 3 equiv), K2S2O8(1 mmol, 2 equiv) and Ru(bpy)3Cl2·6H2O (0.01 mmol, 2 mol%). Themixture was degassed by using standard Schlenk techniques with anoil pump and then filled with nitrogen. A mixed solvent of DCE (5 mL) and H2O (1 mL) was injected into the reaction tube. Then, the reactionmixture was placed at a distance of about 2 cm from a 5 W blue LEDand stirred at room temperature. After 36 h, the reaction mixture wasdiluted with DCM (30 mL) and H2O (25 mL). The aqueous layer wasextracted with DCM (2 × 30 mL). The combined organic layers werewashed with saturated brine (25 mL) and dried over Na2SO4. The organicsolution was concentrated under reduced pressure and purificationwas done by column chromatography on silica gel (200-300mesh) with petroleum ether/EtOAc (5:1 or 10:1, as indicated below)as the eluent to give the pure product 3.4-(Cyclohexylmethyl)-2,4-dimethylisoquinoline-1,3(2H,4H)-dione(3a)16Chromatography: petroleum ether/EtOAc (5:1).Yield: 107 mg (75%); yellow oil.1H NMR (500 MHz, CDCl3): = 8.22 (d, J = 7.5 Hz, 1 H), 7.61-7.58 (m, 1H), 7.39 (t, J = 7.6 Hz, 2 H), 3.35 (s, 3 H), 2.29 (dd, J = 14.0, 7.5 Hz, 1 H),1.87 (dd, J = 14.0, 4.7 Hz, 1 H), 1.53 (s, 3 H), 1.47-1.40 (m, 3 H), 1.23-1.20 (m, 1 H), 1.11 (d, J = 12.7 Hz, 1 H), 0.96-0.70 (m, 6 H).13C{1H} NMR (126 MHz, CDCl3): = 176.0, 163.7, 145.7, 130.6, 130.4,129.0, 128.9, 123.5, 49.6, 49.5, 46.7, 34.8, 34.22, 34.16, 33.0, 32.9,31.6, 31.4, 27.3, 27.2, 26.0, 25.9
53%	With 3-oxo-1λ³-benzo[d][1,2]iodaoxol-1(3H)-yl acetate; Eosin In water monomer; 1,2-dichloro-ethane at 20℃; for 14h; Irradiation;

Reference： [1]Fu, Jiahui; Cai, Xingxing; Liu, Yihuo; Li, Jinghua; Cheng, Dongping; Xu, Xiaoliang [Synthesis, 2022, vol. 54, # 11, p. 2707 - 2723]
[2]Li, Xuezhi; Han, Man-Yi; Wang, Bin; Wang, Lei; Wang, Min [Organic and Biomolecular Chemistry, 2019, vol. 17, # 27, p. 6612 - 6619]

46
[ 4441-56-9 ]
[ 10399-13-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: methanol; water / 2 h / 20 °C / Inert atmosphere 2: dichloromethane; water / 24 h / 25 °C / Inert atmosphere; Sealed tube; Irradiation 3: dichloromethane; methanol; hexane

Reference： [1]Xie, Shasha; Li, Defang; Huang, Hanchu; Zhang, Fuyuan; Chen, Yiyun [Journal of the American Chemical Society, 2019, vol. 141, # 41, p. 16237 - 16242]

47
[ 4441-56-9 ]
[ 4335-77-7 ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 16237 - 16242

48
[ 4441-56-9 ]
[ 2251-76-5 ]
[ 2262-18-2 ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 16237 - 16242

49
[ 4441-56-9 ]
[ 37952-93-5 ]
[ 712-50-5 ]

Yield	Reaction Conditions	Operation in experiment
63%	With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) at 70 - 80℃; for 4h; Inert atmosphere; Ionic liquid;	General procedure for the Suzuki coupling reaction General procedure: An oven dried RB flask equipped with magnetic stirrer bar was charged with the IL solvent (BMIM)BF4 or (BMIM)PF6 (5-7 mL), and NBSac (1 mmol), and the mixture was stirred at r.t. under nitrogen atmosphere for 15-20 minutes. The reaction mixture was then charged with the boronic acid (2 mmol) and Pd(OAc)2 or NiCl2(dppp) (5 mol%) and basic-IL [PAIM][NTf2] (2 mmol). The reaction mixture was heated gently under stirring at 70-80 °C, while monitoring the progress of the reaction TLC. Upon completion, the reaction mixture was cooled to r.t. and the products were extracted 4 times with hexane/ethyl acetate (80:20). The solvent was removed under vacuum and the crude product was chromatographed with hexane/ethyl acetate (70:30) mixture to afford pure compounds.

Reference： [1]Malunavar, Shruti S.; Sutar, Suraj M.; Prabhala, Pavankumar; Kalkhambkar, Rajesh G.; Laali, Kenneth K. [Tetrahedron Letters, 2020, vol. 61, # 24]

50
[ 4441-56-9 ]
1-(2-(2-methoxyphenyl)-1H-benzo[d]imidazol-1-yl)-2-methylprop-2-en-1-one [ No CAS ]
C₂₄H₂₆N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With manganese(III) triacetate dihydrate In acetic acid; acetonitrile at 65℃; for 2h; Electrolysis; Inert atmosphere; Green chemistry;

Reference： [1]Yuan, Yong; Zheng, Yongfu; Xu, Bizhen; Liao, Jiapeng; Bu, Faxiang; Wang, Shengchun; Hu, Jian-Guo; Lei, Aiwen [ACS Catalysis, 2020, vol. 10, # 12, p. 6676 - 6681]

51
[ 4441-56-9 ]
C₁₉H₁₈N₂O [ No CAS ]
C₂₅H₂₈N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With manganese(III) triacetate dihydrate In acetic acid; acetonitrile at 65℃; for 2h; Electrolysis; Inert atmosphere; Green chemistry;

Reference： [1]Yuan, Yong; Zheng, Yongfu; Xu, Bizhen; Liao, Jiapeng; Bu, Faxiang; Wang, Shengchun; Hu, Jian-Guo; Lei, Aiwen [ACS Catalysis, 2020, vol. 10, # 12, p. 6676 - 6681]

52
[ 4441-56-9 ]
2-methyl-1-(2-phenyl-1H-benzo[d]imidazol-1-yl)prop-2-en-1-one [ No CAS ]
5-(cyclohexylmethyl)-5-methylbenzo[4,5]imidazo[2,1-a]-isoquinolin-6(5H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With manganese(III) triacetate dihydrate In acetic acid; acetonitrile at 65℃; for 2h; Electrolysis; Inert atmosphere; Green chemistry;
47%	With oxygen In ethyl acetate at 120℃; for 16h; Sealed tube; Schlenk technique;

Reference： [1]Yuan, Yong; Zheng, Yongfu; Xu, Bizhen; Liao, Jiapeng; Bu, Faxiang; Wang, Shengchun; Hu, Jian-Guo; Lei, Aiwen [ACS Catalysis, 2020, vol. 10, # 12, p. 6676 - 6681]
[2]Pan, Changduo; Yuan, Cheng; Yu, Jin-Tao [Advanced Synthesis and Catalysis, 2021, vol. 363, # 21, p. 4889 - 4893]

53
[ 99-99-0 ]
[ 4441-56-9 ]
N-(p-tolyl)cyclohexanesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With sodium metabisulfite; lithium phosphate; choline chloride In N,N-dimethyl-formamide at 130℃; for 10h; Inert atmosphere;	31 Example 31Synthesis of compound 33 Add 1-methyl-4-nitrobenzene (0.2mmol), sodium metabisulfite (0.6mmol, 3.0 equiv), cyclohexylboronic acid (0.3mmol, 1.5equiv) to the reaction tube,Choline chloride (0.2mmol, 1.0equiv), lithium phosphate (0.4mmol, 2.0equiv),Evacuate and change nitrogen three times and add solvent DMF (2.0mL),The reaction system was heated to 130°C for 10 hours. After all the nitro compounds were completely converted, the reaction system was cooled to room temperature, quenched with water, and extracted with ethyl acetate (10 mL*3).Dry with anhydrous sodium sulfate, filter, concentrate,Column chromatography separation yielded the purified target product 33 (58%).
58%	With sodium metabisulfite; lithium phosphate; choline chloride; water In N,N-dimethyl-formamide at 130℃; for 10h; Schlenk technique; Inert atmosphere;

Reference： [1]Current Patent Assignee: EAST CHINA NORMAL UNIVERSITY - CN111393336, 2020, A Location in patent: Paragraph 0171-0174
[2]Li, Yaping; Wang, Ming; Jiang, Xuefeng [Chinese Journal of Chemistry, 2020, vol. 38, # 12, p. 1521 - 1525]

54
[ 4441-56-9 ]
[ 13480-36-9 ]
2-cyclohexyl-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%	In 1,4-dioxane at 70℃; for 24h; Dean-Stark;
26%	In 1,4-dioxane at 70℃; for 24h;

Reference： [1]Kelly, Aidan M.; Chen, Peng-Jui; Klubnick, Jenna; Blair, Daniel J.; Burke, Martin D. [Organic Letters, 2020, vol. 22, # 24, p. 9408 - 9414]
[2]Blair, Daniel J.; Burke, Martin D.; Chen, Peng-Jui; Kelly, Aidan M. [Organic Syntheses, 2022, vol. 99, p. 92 - 112]

55
((E)-1-Trifluoromethyl-buta-1,3-dienyl)-benzene [ No CAS ]
[ 4441-56-9 ]
(E)-(5-cyclohexyl-1,1-difluoropenta-1,3-dien-2-yl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	With 1,4-diaza-bicyclo[2.2.2]octane; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; caesium carbonate In dichloromethane at 20℃; Inert atmosphere; Irradiation;	General Procedure for amplification experiment General procedure: Under the protection of nitrogen, [Ir(dFCF3ppy)2(dtbbpy)]PF6 (0.025 mmol, 0.5mol%), 1a (5 mmol), 2a (10 mmol), DABCO (0.2 equiv), Cs2CO3 (2 equiv) and anhydrous DCM (50 ml) were added into a 100 ml three port flask. The reaction mixture was placed at a distance of about 5 cm from 45 w CFL, stirred at room temperature, and the reaction was tracked by TLC. After the reaction, H2O (100 ml) was added and the water layer was extracted with DCM (3 × 50 ml). The organic phase was combined, dried with anhydrous sodium sulfate, filtered, and the solvent was removed by rotary evaporator. The product 3a (1.03 g) was obtained by column chromatography (PE).

Reference： [1]Chen, Yuefeng; Ni, Niannian; Cheng, Dongping; Xu, Xiaoliang [Tetrahedron Letters, 2020, vol. 61, # 43]

56
[ 4441-56-9 ]
[ 69843-10-3 ]
1-chloro-4-(3-cyclohexyl-1,1-difluoroprop-1-en-2-yl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With 1,4-diaza-bicyclo[2.2.2]octane; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; caesium carbonate In dichloromethane at 20℃; Inert atmosphere; Irradiation;	General Procedure for amplification experiment Under the protection of nitrogen, [Ir(dFCF3ppy)2(dtbbpy)]PF6 (0.025 mmol, 0.5mol%), 1a (5 mmol), 2a (10 mmol), DABCO (0.2 equiv), Cs2CO3 (2 equiv) and anhydrous DCM (50 ml) were added into a 100 ml three port flask. The reaction mixture was placed at a distance of about 5 cm from 45 w CFL, stirred at room temperature, and the reaction was tracked by TLC. After the reaction, H2O (100 ml) was added and the water layer was extracted with DCM (3 × 50 ml). The organic phase was combined, dried with anhydrous sodium sulfate, filtered, and the solvent was removed by rotary evaporator. The product 3a (1.03 g) was obtained by column chromatography (PE). 1-chloro-4-(3-cyclohexyl-1,1-difluoroprop-1-en-2-yl)benzene(3a). 85% yield, colorless oil; 1H NMR (500 MHz, CDCl3) δ 7.34-7.27 (m, 2H), 7.24-7.21 (m, 2H), 2.26-2.22 (m, 2H), 1.68-1.58 (m, 5H), 1.25-1.17 (m, 1H), 1.14-1.06 (m, 3H), 0.94-0.86 (m, 2H).13C NMR (126 MHz, CDCl3) δ 154.01 (dd, J = 290.7, 286.6 Hz), 132.94, 132.60 (dd, J = 4.7, 3.2 Hz), 129.60 (t, J = 3.3 Hz), 128.63, 90.36 (dd, J = 22.8, 12.4 Hz), 35.71, 35.10, 32.85, 26.38, 26.05. 19F NMR (376 MHz, CDCl3) δ -90.51 (d, J = 42.5 Hz, 1F), -91.06 (d, J = 42.4 Hz, 1F). HRMS (EI) calcd for C15H17ClF2 (M+) 270.0987, found: 270.0991.

Reference： [1]Chen, Yuefeng; Ni, Niannian; Cheng, Dongping; Xu, Xiaoliang [Tetrahedron Letters, 2020, vol. 61, # 43]

57
[ 4441-56-9 ]
[ 69843-09-0 ]
1-(3-cyclohexyl-1,1-difluoroprop-1-en-2-yl)-4-methylbenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With 1,4-diaza-bicyclo[2.2.2]octane; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; caesium carbonate In dichloromethane at 20℃; Inert atmosphere; Irradiation;	General Procedure for amplification experiment General procedure: Under the protection of nitrogen, [Ir(dFCF3ppy)2(dtbbpy)]PF6 (0.025 mmol, 0.5mol%), 1a (5 mmol), 2a (10 mmol), DABCO (0.2 equiv), Cs2CO3 (2 equiv) and anhydrous DCM (50 ml) were added into a 100 ml three port flask. The reaction mixture was placed at a distance of about 5 cm from 45 w CFL, stirred at room temperature, and the reaction was tracked by TLC. After the reaction, H2O (100 ml) was added and the water layer was extracted with DCM (3 × 50 ml). The organic phase was combined, dried with anhydrous sodium sulfate, filtered, and the solvent was removed by rotary evaporator. The product 3a (1.03 g) was obtained by column chromatography (PE).

Reference： [1]Chen, Yuefeng; Ni, Niannian; Cheng, Dongping; Xu, Xiaoliang [Tetrahedron Letters, 2020, vol. 61, # 43]

58
[ 4441-56-9 ]
1-methyl-3-(1,1,1-trifluoroprop-2-en-2-yl)benzene [ No CAS ]
1-(3-cyclohexyl-1,1-difluoroprop-1-en-2-yl)-3-methylbenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With 1,4-diaza-bicyclo[2.2.2]octane; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; caesium carbonate In dichloromethane at 20℃; Inert atmosphere; Irradiation;	General Procedure for amplification experiment General procedure: Under the protection of nitrogen, [Ir(dFCF3ppy)2(dtbbpy)]PF6 (0.025 mmol, 0.5mol%), 1a (5 mmol), 2a (10 mmol), DABCO (0.2 equiv), Cs2CO3 (2 equiv) and anhydrous DCM (50 ml) were added into a 100 ml three port flask. The reaction mixture was placed at a distance of about 5 cm from 45 w CFL, stirred at room temperature, and the reaction was tracked by TLC. After the reaction, H2O (100 ml) was added and the water layer was extracted with DCM (3 × 50 ml). The organic phase was combined, dried with anhydrous sodium sulfate, filtered, and the solvent was removed by rotary evaporator. The product 3a (1.03 g) was obtained by column chromatography (PE).

Reference： [1]Chen, Yuefeng; Ni, Niannian; Cheng, Dongping; Xu, Xiaoliang [Tetrahedron Letters, 2020, vol. 61, # 43]

59
[ 4441-56-9 ]
1,3-dimethyl-5-(1,1,1-trifluoroprop-2-en-2-yl)benzene [ No CAS ]
1-(3-cyclohexyl-1,1-difluoroprop-1-en-2-yl)-3,5-dimethylbenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With 1,4-diaza-bicyclo[2.2.2]octane; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; caesium carbonate In dichloromethane at 20℃; Inert atmosphere; Irradiation;	General Procedure for amplification experiment General procedure: Under the protection of nitrogen, [Ir(dFCF3ppy)2(dtbbpy)]PF6 (0.025 mmol, 0.5mol%), 1a (5 mmol), 2a (10 mmol), DABCO (0.2 equiv), Cs2CO3 (2 equiv) and anhydrous DCM (50 ml) were added into a 100 ml three port flask. The reaction mixture was placed at a distance of about 5 cm from 45 w CFL, stirred at room temperature, and the reaction was tracked by TLC. After the reaction, H2O (100 ml) was added and the water layer was extracted with DCM (3 × 50 ml). The organic phase was combined, dried with anhydrous sodium sulfate, filtered, and the solvent was removed by rotary evaporator. The product 3a (1.03 g) was obtained by column chromatography (PE).

Reference： [1]Chen, Yuefeng; Ni, Niannian; Cheng, Dongping; Xu, Xiaoliang [Tetrahedron Letters, 2020, vol. 61, # 43]

60
[ 4441-56-9 ]
1-isopropyl-4-(1,1,1-trifluoroprop-2-en-2-yl)benzene [ No CAS ]
1-(3-cyclohexyl-1,1-difluoroprop-1-en-2-yl)-4-isopropylbenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With 1,4-diaza-bicyclo[2.2.2]octane; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; caesium carbonate In dichloromethane at 20℃; Inert atmosphere; Irradiation;	General Procedure for amplification experiment General procedure: Under the protection of nitrogen, [Ir(dFCF3ppy)2(dtbbpy)]PF6 (0.025 mmol, 0.5mol%), 1a (5 mmol), 2a (10 mmol), DABCO (0.2 equiv), Cs2CO3 (2 equiv) and anhydrous DCM (50 ml) were added into a 100 ml three port flask. The reaction mixture was placed at a distance of about 5 cm from 45 w CFL, stirred at room temperature, and the reaction was tracked by TLC. After the reaction, H2O (100 ml) was added and the water layer was extracted with DCM (3 × 50 ml). The organic phase was combined, dried with anhydrous sodium sulfate, filtered, and the solvent was removed by rotary evaporator. The product 3a (1.03 g) was obtained by column chromatography (PE).

Reference： [1]Chen, Yuefeng; Ni, Niannian; Cheng, Dongping; Xu, Xiaoliang [Tetrahedron Letters, 2020, vol. 61, # 43]

61
[ 4441-56-9 ]
[ 69843-08-9 ]
1-(3-cyclohexyl-1,1-difluoroprop-1-en-2-yl)-4-methoxybenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With 1,4-diaza-bicyclo[2.2.2]octane; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; caesium carbonate In dichloromethane at 20℃; Inert atmosphere; Irradiation;	General Procedure for amplification experiment General procedure: Under the protection of nitrogen, [Ir(dFCF3ppy)2(dtbbpy)]PF6 (0.025 mmol, 0.5mol%), 1a (5 mmol), 2a (10 mmol), DABCO (0.2 equiv), Cs2CO3 (2 equiv) and anhydrous DCM (50 ml) were added into a 100 ml three port flask. The reaction mixture was placed at a distance of about 5 cm from 45 w CFL, stirred at room temperature, and the reaction was tracked by TLC. After the reaction, H2O (100 ml) was added and the water layer was extracted with DCM (3 × 50 ml). The organic phase was combined, dried with anhydrous sodium sulfate, filtered, and the solvent was removed by rotary evaporator. The product 3a (1.03 g) was obtained by column chromatography (PE).

Reference： [1]Chen, Yuefeng; Ni, Niannian; Cheng, Dongping; Xu, Xiaoliang [Tetrahedron Letters, 2020, vol. 61, # 43]

62
[ 4441-56-9 ]
[ 946614-13-7 ]
1-(3-cyclohexyl-1,1-difluoroprop-1-en-2-yl)-3-methoxybenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With 1,4-diaza-bicyclo[2.2.2]octane; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; caesium carbonate In dichloromethane at 20℃; Inert atmosphere; Irradiation;	General Procedure for amplification experiment General procedure: Under the protection of nitrogen, [Ir(dFCF3ppy)2(dtbbpy)]PF6 (0.025 mmol, 0.5mol%), 1a (5 mmol), 2a (10 mmol), DABCO (0.2 equiv), Cs2CO3 (2 equiv) and anhydrous DCM (50 ml) were added into a 100 ml three port flask. The reaction mixture was placed at a distance of about 5 cm from 45 w CFL, stirred at room temperature, and the reaction was tracked by TLC. After the reaction, H2O (100 ml) was added and the water layer was extracted with DCM (3 × 50 ml). The organic phase was combined, dried with anhydrous sodium sulfate, filtered, and the solvent was removed by rotary evaporator. The product 3a (1.03 g) was obtained by column chromatography (PE).

Reference： [1]Chen, Yuefeng; Ni, Niannian; Cheng, Dongping; Xu, Xiaoliang [Tetrahedron Letters, 2020, vol. 61, # 43]

63
[ 4441-56-9 ]
1-methoxy-2-(1,1,1-trifluoroprop-2-en-2-yl)benzene [ No CAS ]
1-(3-cyclohexyl-1,1-difluoroprop-1-en-2-yl)-2-methoxybenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With 1,4-diaza-bicyclo[2.2.2]octane; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; caesium carbonate In dichloromethane at 20℃; Inert atmosphere; Irradiation;	General Procedure for amplification experiment General procedure: Under the protection of nitrogen, [Ir(dFCF3ppy)2(dtbbpy)]PF6 (0.025 mmol, 0.5mol%), 1a (5 mmol), 2a (10 mmol), DABCO (0.2 equiv), Cs2CO3 (2 equiv) and anhydrous DCM (50 ml) were added into a 100 ml three port flask. The reaction mixture was placed at a distance of about 5 cm from 45 w CFL, stirred at room temperature, and the reaction was tracked by TLC. After the reaction, H2O (100 ml) was added and the water layer was extracted with DCM (3 × 50 ml). The organic phase was combined, dried with anhydrous sodium sulfate, filtered, and the solvent was removed by rotary evaporator. The product 3a (1.03 g) was obtained by column chromatography (PE).

Reference： [1]Chen, Yuefeng; Ni, Niannian; Cheng, Dongping; Xu, Xiaoliang [Tetrahedron Letters, 2020, vol. 61, # 43]

64
[ 4441-56-9 ]
methyl(4-(3,3,3-trifluoroprop-1-en-2-yl)phenyl)sulfane [ No CAS ]
(4-(3-cyclohexyl-1,1-difluoroprop-1-en-2-yl)phenyl)(methyl)sulfane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With 1,4-diaza-bicyclo[2.2.2]octane; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; caesium carbonate In dichloromethane at 20℃; Inert atmosphere; Irradiation;	General Procedure for amplification experiment General procedure: Under the protection of nitrogen, [Ir(dFCF3ppy)2(dtbbpy)]PF6 (0.025 mmol, 0.5mol%), 1a (5 mmol), 2a (10 mmol), DABCO (0.2 equiv), Cs2CO3 (2 equiv) and anhydrous DCM (50 ml) were added into a 100 ml three port flask. The reaction mixture was placed at a distance of about 5 cm from 45 w CFL, stirred at room temperature, and the reaction was tracked by TLC. After the reaction, H2O (100 ml) was added and the water layer was extracted with DCM (3 × 50 ml). The organic phase was combined, dried with anhydrous sodium sulfate, filtered, and the solvent was removed by rotary evaporator. The product 3a (1.03 g) was obtained by column chromatography (PE).

Reference： [1]Chen, Yuefeng; Ni, Niannian; Cheng, Dongping; Xu, Xiaoliang [Tetrahedron Letters, 2020, vol. 61, # 43]

65
[ 4441-56-9 ]
C₁₁H₉F₃ [ No CAS ]
1-(3-cyclohexyl-1,1-difluoroprop-1-en-2-yl)-4-vinylbenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With 1,4-diaza-bicyclo[2.2.2]octane; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; caesium carbonate In dichloromethane at 20℃; Inert atmosphere; Irradiation;	General Procedure for amplification experiment General procedure: Under the protection of nitrogen, [Ir(dFCF3ppy)2(dtbbpy)]PF6 (0.025 mmol, 0.5mol%), 1a (5 mmol), 2a (10 mmol), DABCO (0.2 equiv), Cs2CO3 (2 equiv) and anhydrous DCM (50 ml) were added into a 100 ml three port flask. The reaction mixture was placed at a distance of about 5 cm from 45 w CFL, stirred at room temperature, and the reaction was tracked by TLC. After the reaction, H2O (100 ml) was added and the water layer was extracted with DCM (3 × 50 ml). The organic phase was combined, dried with anhydrous sodium sulfate, filtered, and the solvent was removed by rotary evaporator. The product 3a (1.03 g) was obtained by column chromatography (PE).

Reference： [1]Chen, Yuefeng; Ni, Niannian; Cheng, Dongping; Xu, Xiaoliang [Tetrahedron Letters, 2020, vol. 61, # 43]

66
[ 4441-56-9 ]
[ 384-64-5 ]
(3-cyclohexyl-1,1-difluoroprop-1-en-2-yl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With 1,4-diaza-bicyclo[2.2.2]octane; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; caesium carbonate In dichloromethane at 20℃; Inert atmosphere; Irradiation;	General Procedure for amplification experiment General procedure: Under the protection of nitrogen, [Ir(dFCF3ppy)2(dtbbpy)]PF6 (0.025 mmol, 0.5mol%), 1a (5 mmol), 2a (10 mmol), DABCO (0.2 equiv), Cs2CO3 (2 equiv) and anhydrous DCM (50 ml) were added into a 100 ml three port flask. The reaction mixture was placed at a distance of about 5 cm from 45 w CFL, stirred at room temperature, and the reaction was tracked by TLC. After the reaction, H2O (100 ml) was added and the water layer was extracted with DCM (3 × 50 ml). The organic phase was combined, dried with anhydrous sodium sulfate, filtered, and the solvent was removed by rotary evaporator. The product 3a (1.03 g) was obtained by column chromatography (PE).

Reference： [1]Chen, Yuefeng; Ni, Niannian; Cheng, Dongping; Xu, Xiaoliang [Tetrahedron Letters, 2020, vol. 61, # 43]

67
[ 4441-56-9 ]
[ 1601477-35-3 ]
4-(3-cyclohexyl-1,1-difluoroprop-1-en-2-yl)-1,1'-biphenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With 1,4-diaza-bicyclo[2.2.2]octane; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; caesium carbonate In dichloromethane at 20℃; Inert atmosphere; Irradiation;	General Procedure for amplification experiment General procedure: Under the protection of nitrogen, [Ir(dFCF3ppy)2(dtbbpy)]PF6 (0.025 mmol, 0.5mol%), 1a (5 mmol), 2a (10 mmol), DABCO (0.2 equiv), Cs2CO3 (2 equiv) and anhydrous DCM (50 ml) were added into a 100 ml three port flask. The reaction mixture was placed at a distance of about 5 cm from 45 w CFL, stirred at room temperature, and the reaction was tracked by TLC. After the reaction, H2O (100 ml) was added and the water layer was extracted with DCM (3 × 50 ml). The organic phase was combined, dried with anhydrous sodium sulfate, filtered, and the solvent was removed by rotary evaporator. The product 3a (1.03 g) was obtained by column chromatography (PE).
74%	With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile In N,N-dimethyl acetamide at 20℃; for 20h; Irradiation;

Reference： [1]Chen, Yuefeng; Ni, Niannian; Cheng, Dongping; Xu, Xiaoliang [Tetrahedron Letters, 2020, vol. 61, # 43]
[2]Ranjan, Prabhat; Pillitteri, Serena; Coppola, Guglielmo; Oliva, Monica; Van der Eycken, Erik V.; Sharma, Upendra K. [ACS Catalysis, 2021, vol. 11, # 17, p. 10862 - 10870]

68
[ 4441-56-9 ]
[ 655-29-8 ]
1-(3-cyclohexyl-1,1-difluoroprop-1-en-2-yl)-4-fluorobenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With 1,4-diaza-bicyclo[2.2.2]octane; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; caesium carbonate In dichloromethane at 20℃; Inert atmosphere; Irradiation;	General Procedure for amplification experiment General procedure: Under the protection of nitrogen, [Ir(dFCF3ppy)2(dtbbpy)]PF6 (0.025 mmol, 0.5mol%), 1a (5 mmol), 2a (10 mmol), DABCO (0.2 equiv), Cs2CO3 (2 equiv) and anhydrous DCM (50 ml) were added into a 100 ml three port flask. The reaction mixture was placed at a distance of about 5 cm from 45 w CFL, stirred at room temperature, and the reaction was tracked by TLC. After the reaction, H2O (100 ml) was added and the water layer was extracted with DCM (3 × 50 ml). The organic phase was combined, dried with anhydrous sodium sulfate, filtered, and the solvent was removed by rotary evaporator. The product 3a (1.03 g) was obtained by column chromatography (PE).

Reference： [1]Chen, Yuefeng; Ni, Niannian; Cheng, Dongping; Xu, Xiaoliang [Tetrahedron Letters, 2020, vol. 61, # 43]

69
[ 4441-56-9 ]
[ 136476-20-5 ]
1-bromo-4-(3-cyclohexyl-1,1-difluoroprop-1-en-2-yl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With 1,4-diaza-bicyclo[2.2.2]octane; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; caesium carbonate In dichloromethane at 20℃; Inert atmosphere; Irradiation;	General Procedure for amplification experiment General procedure: Under the protection of nitrogen, [Ir(dFCF3ppy)2(dtbbpy)]PF6 (0.025 mmol, 0.5mol%), 1a (5 mmol), 2a (10 mmol), DABCO (0.2 equiv), Cs2CO3 (2 equiv) and anhydrous DCM (50 ml) were added into a 100 ml three port flask. The reaction mixture was placed at a distance of about 5 cm from 45 w CFL, stirred at room temperature, and the reaction was tracked by TLC. After the reaction, H2O (100 ml) was added and the water layer was extracted with DCM (3 × 50 ml). The organic phase was combined, dried with anhydrous sodium sulfate, filtered, and the solvent was removed by rotary evaporator. The product 3a (1.03 g) was obtained by column chromatography (PE).
52%	With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile In N,N-dimethyl acetamide at 20℃; for 20h; Irradiation;

Reference： [1]Chen, Yuefeng; Ni, Niannian; Cheng, Dongping; Xu, Xiaoliang [Tetrahedron Letters, 2020, vol. 61, # 43]
[2]Ranjan, Prabhat; Pillitteri, Serena; Coppola, Guglielmo; Oliva, Monica; Van der Eycken, Erik V.; Sharma, Upendra K. [ACS Catalysis, 2021, vol. 11, # 17, p. 10862 - 10870]

70
[ 4441-56-9 ]
[ 136476-29-4 ]
2-(3-cyclohexyl-1,1-difluoroprop-1-en-2-yl)naphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With 1,4-diaza-bicyclo[2.2.2]octane; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; caesium carbonate In dichloromethane at 20℃; Inert atmosphere; Irradiation;	General Procedure for amplification experiment General procedure: Under the protection of nitrogen, [Ir(dFCF3ppy)2(dtbbpy)]PF6 (0.025 mmol, 0.5mol%), 1a (5 mmol), 2a (10 mmol), DABCO (0.2 equiv), Cs2CO3 (2 equiv) and anhydrous DCM (50 ml) were added into a 100 ml three port flask. The reaction mixture was placed at a distance of about 5 cm from 45 w CFL, stirred at room temperature, and the reaction was tracked by TLC. After the reaction, H2O (100 ml) was added and the water layer was extracted with DCM (3 × 50 ml). The organic phase was combined, dried with anhydrous sodium sulfate, filtered, and the solvent was removed by rotary evaporator. The product 3a (1.03 g) was obtained by column chromatography (PE).

Reference： [1]Chen, Yuefeng; Ni, Niannian; Cheng, Dongping; Xu, Xiaoliang [Tetrahedron Letters, 2020, vol. 61, # 43]

71
[ 4441-56-9 ]
[ 136476-28-3 ]
1-(3-cyclohexyl-1,1-difluoroprop-1-en-2-yl)naphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With 1,4-diaza-bicyclo[2.2.2]octane; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; caesium carbonate In dichloromethane at 20℃; Inert atmosphere; Irradiation;	General Procedure for amplification experiment General procedure: Under the protection of nitrogen, [Ir(dFCF3ppy)2(dtbbpy)]PF6 (0.025 mmol, 0.5mol%), 1a (5 mmol), 2a (10 mmol), DABCO (0.2 equiv), Cs2CO3 (2 equiv) and anhydrous DCM (50 ml) were added into a 100 ml three port flask. The reaction mixture was placed at a distance of about 5 cm from 45 w CFL, stirred at room temperature, and the reaction was tracked by TLC. After the reaction, H2O (100 ml) was added and the water layer was extracted with DCM (3 × 50 ml). The organic phase was combined, dried with anhydrous sodium sulfate, filtered, and the solvent was removed by rotary evaporator. The product 3a (1.03 g) was obtained by column chromatography (PE).

Reference： [1]Chen, Yuefeng; Ni, Niannian; Cheng, Dongping; Xu, Xiaoliang [Tetrahedron Letters, 2020, vol. 61, # 43]

72
[ 4441-56-9 ]
2-(3,3,3-trifluoroprop-1-en-2-yl)thiophene [ No CAS ]
2-(3-cyclohexyl-1,1-difluoroprop-1-en-2-yl)thiophene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With 1,4-diaza-bicyclo[2.2.2]octane; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; caesium carbonate In dichloromethane at 20℃; Inert atmosphere; Irradiation;	General Procedure for amplification experiment General procedure: Under the protection of nitrogen, [Ir(dFCF3ppy)2(dtbbpy)]PF6 (0.025 mmol, 0.5mol%), 1a (5 mmol), 2a (10 mmol), DABCO (0.2 equiv), Cs2CO3 (2 equiv) and anhydrous DCM (50 ml) were added into a 100 ml three port flask. The reaction mixture was placed at a distance of about 5 cm from 45 w CFL, stirred at room temperature, and the reaction was tracked by TLC. After the reaction, H2O (100 ml) was added and the water layer was extracted with DCM (3 × 50 ml). The organic phase was combined, dried with anhydrous sodium sulfate, filtered, and the solvent was removed by rotary evaporator. The product 3a (1.03 g) was obtained by column chromatography (PE).

Reference： [1]Chen, Yuefeng; Ni, Niannian; Cheng, Dongping; Xu, Xiaoliang [Tetrahedron Letters, 2020, vol. 61, # 43]

73
[ 4441-56-9 ]
[ 2942-14-5 ]
2-cyclohexyl-5-methoxybenzo[d]thiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; oxygen; trifluoroacetic acid In 1,2-dichloro-ethane at 20℃; for 24h; Sealed tube; Irradiation;

Reference： [1]Dong, Jianyang; Yue, Fuyang; Song, Hongjian; Liu, Yuxiu; Wang, Qingmin [Chemical Communications, 2020, vol. 56, # 83, p. 12652 - 12655]

74
[ 4441-56-9 ]
[ 31637-97-5 ]
[ 2497686-91-4 ]

Yield	Reaction Conditions	Operation in experiment
65%	With [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; oxygen; trifluoroacetic acid In 1,2-dichloro-ethane at 20℃; for 24h; Sealed tube; Irradiation;

Reference： [1]Dong, Jianyang; Yue, Fuyang; Song, Hongjian; Liu, Yuxiu; Wang, Qingmin [Chemical Communications, 2020, vol. 56, # 83, p. 12652 - 12655]

75
[ 4441-56-9 ]
[ 464-72-2 ]
2-cyclohexyl-4,4,5,5-tetraphenyl-1,3,2-dioxaborolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With magnesium sulfate In tetrahydrofuran at 65℃; for 36h;

Reference： [1]Fasano, Valerio; McFord, Aidan W.; Butts, Craig P.; Collins, Beatrice S. L.; Fey, Natalie; Alder, Roger W.; Aggarwal, Varinder K. [Angewandte Chemie - International Edition, 2020, vol. 59, # 50, p. 22403 - 22407][Angew. Chem., 2020, vol. 132, # 50, p. 22589 - 22593]

76
[ 4441-56-9 ]
2-bromo-N,N-bis(4-methoxybenzyl)-6-(prop-1-en-2-yl)pyridin-4-amine [ No CAS ]
2-(cyclohex-1-en-1-yl)-N,N-bis(4-methoxybenzyl)-6-(prop-1-en-2-yl)pyridine-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,4-dioxane at 90℃; for 2h;	131.131-1 Step 131-1: 2-(cyclohex-1-en-1-yl)-N,N-bis(4-methoxybenzyl)-6-(prop-1-en-2-yl)pyridine- 4-amine. Heated at 90 for 2h, using 2-bromo-N,N-bis(4-methoxybenzyl)-6-(prop-1-en-2-yl)pyridin-4-amine (0.595g, 1.31mmol ), cyclohexylboronic acid (0.182g, 1.44mmol), dioxane (22.0mL), water (5.0mL), potassium carbonate (0.543g, 3.93mmol) and Pd(PPh3)2Cl2 (0.092g, 0.13mmol). The crude product was purified by silica flash column chromatography (4:1 hexane:EtOAc) to give the title compound as a colorless oil (0.360 g, 60%).

Reference： [1]Current Patent Assignee: UNIVERSITY OF MANCHESTER - CN112119077, 2020, A Location in patent: Paragraph 0802-0803

77
[ 108-85-0 ]
[ 5419-55-6 ]
[ 7732-18-5 ]
[ 4441-56-9 ]

Yield	Reaction Conditions	Operation in experiment
51%	Stage #1: 1-bromocyclohexane; Triisopropyl borate With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 15h; Inert atmosphere; Stage #2: water In tetrahydrofuran	3 Example 3 Add 5mmol 1-bromocyclohexane to a 150mL two-necked flask, and add 80mL of tetrahydrofuran solvent (THF) after removing water and oxygen under nitrogen atmosphere. Then add 5.5mmol boric acid ester, stir well and place it at -78 °C, then add 5.1mmol n-butyllithium dropwise, react at -78 °C for 3h, then return to room temperature for 12h. After the completion of the reaction, the reaction solution was poured into water, extracted with dichloromethane 3 times, then dried with anhydrous MgSO4, filtered, and the solvent was removed by rotary evaporation, and the silica gel column was used for separation and purification. Using n-hexane/dichloromethane as the eluent, the solvent was removed by rotary evaporation and drying to obtain cyclohexylboronic acid with a yield of 51%.

Reference： [1]Current Patent Assignee: TCL TECHNOLOGY GROUP CORPORATION - CN112321630, 2021, A Location in patent: Paragraph 0063; 0119; 0120

78
[ 6479-18-1 ]
[ 4441-56-9 ]
3-cyclohexyl-1-methylquinoxaline-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With air In N,N-dimethyl-formamide at 20℃; for 12h; Irradiation;	2.1 Typical experimental procedure for the synthesis of 3-alkylquinoxalin-2(1H)-ones (3a-3ab) General procedure: A 10 mL oven-dried reaction vessel equipped with a magnetic stirrer was charged with quinoxalin-2(1H)-one (1, 0.20 mmol), alkylboronic acid (2, 0.40 mmol) and N,N-dimethylformamide (DMF, 2.0 mL). The reaction vessel was exposed to blue LED (440-445 nm, 1.5 W) irradiation at room temperature in air with stirring for 12 h. After completion of the reaction, the mixture was diluted with water and extracted with ethyl acetate, the organic layer was combined, dried over by anhydrous Na 2 SO 4 , and filtered, then concentrated to yield the crude product, which was further purified by flash chromatography (silica gel, petroleum ether/ethyl acetate = 10:1) to give the desired product 3a-3ad.
84%	With tert-butylammonium hexafluorophosphate(V); trifluoroacetic acid In N,N-dimethyl-formamide at 80℃; for 8h; Electrolysis;
73%	With acetic acid In acetone at 120℃; for 16h; chemoselective reaction;	General procedure for the alkylation of quinoxalin-2(1H)-ones with alkylboronic acids General procedure: To a 15 mL tube was charged with 1 (0.2 mmol), 2 (0.4 mmol), CH3CO2H (25 mol%), and acetone (2 mL). The tube was heated to 120 oC in the heating block for 16 h. The reaction mixture was then quenched with saturated NaHCO3 solution and extracted with EtOAc. The organic layer was dried over anhydrous MgSO4, and the solvent was removed under reduced pressure. The crude product was further purified by silica gel column chromatography (200-300 mesh silica gel, PE/EA/DCM = 4:1:1) to afford product 4.

Reference： [1]Yao, Lingling; Zhu, Defeng; Wang, Lei; Liu, Jie; Zhang, Yicheng; Li, Pinhua [Chinese Chemical Letters, 2021, vol. 32, # 12, p. 4033 - 4037]
[2]Niu, Kaikai; Hao, Yanke; Song, Lingyun; Liu, Yuxiu; Wang, Qingmin [Green Chemistry, 2021, vol. 23, # 1, p. 302 - 306]
[3]Zhang, Hongdou; Xu, Jun; Ouyang, Yani; Yue, Xiaoguang; Zhou, Chenxin; Ni, Zhigang; Li, Wanmei [Chinese Chemical Letters, 2022, vol. 33, # 4, p. 2036 - 2040]

79
[ 4441-56-9 ]
[ 65845-74-1 ]
6-chloro-3-cyclohexyl-1-methylquinoxalin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With air In N,N-dimethyl-formamide at 20℃; for 12h; Irradiation;	2.1 Typical experimental procedure for the synthesis of 3-alkylquinoxalin-2(1H)-ones (3a-3ab) General procedure: A 10 mL oven-dried reaction vessel equipped with a magnetic stirrer was charged with quinoxalin-2(1H)-one (1, 0.20 mmol), alkylboronic acid (2, 0.40 mmol) and N,N-dimethylformamide (DMF, 2.0 mL). The reaction vessel was exposed to blue LED (440-445 nm, 1.5 W) irradiation at room temperature in air with stirring for 12 h. After completion of the reaction, the mixture was diluted with water and extracted with ethyl acetate, the organic layer was combined, dried over by anhydrous Na 2 SO 4 , and filtered, then concentrated to yield the crude product, which was further purified by flash chromatography (silica gel, petroleum ether/ethyl acetate = 10:1) to give the desired product 3a-3ad.
82%	With tert-butylammonium hexafluorophosphate(V); trifluoroacetic acid In N,N-dimethyl-formamide at 80℃; for 8h; Electrolysis;

Reference： [1]Yao, Lingling; Zhu, Defeng; Wang, Lei; Liu, Jie; Zhang, Yicheng; Li, Pinhua [Chinese Chemical Letters, 2021, vol. 32, # 12, p. 4033 - 4037]
[2]Niu, Kaikai; Hao, Yanke; Song, Lingyun; Liu, Yuxiu; Wang, Qingmin [Green Chemistry, 2021, vol. 23, # 1, p. 302 - 306]

80
[ 4441-56-9 ]
6-fluoro-1-methylquinoxalin-2(1Η)-one [ No CAS ]
3-cyclohexyl-6-fluoro-1-methylquinoxalin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With air In N,N-dimethyl-formamide at 20℃; for 12h; Irradiation;	2.1 Typical experimental procedure for the synthesis of 3-alkylquinoxalin-2(1H)-ones (3a-3ab) General procedure: A 10 mL oven-dried reaction vessel equipped with a magnetic stirrer was charged with quinoxalin-2(1H)-one (1, 0.20 mmol), alkylboronic acid (2, 0.40 mmol) and N,N-dimethylformamide (DMF, 2.0 mL). The reaction vessel was exposed to blue LED (440-445 nm, 1.5 W) irradiation at room temperature in air with stirring for 12 h. After completion of the reaction, the mixture was diluted with water and extracted with ethyl acetate, the organic layer was combined, dried over by anhydrous Na 2 SO 4 , and filtered, then concentrated to yield the crude product, which was further purified by flash chromatography (silica gel, petroleum ether/ethyl acetate = 10:1) to give the desired product 3a-3ad.
54%	With tert-butylammonium hexafluorophosphate(V); trifluoroacetic acid In N,N-dimethyl-formamide at 80℃; for 8h; Electrolysis;

Reference： [1]Yao, Lingling; Zhu, Defeng; Wang, Lei; Liu, Jie; Zhang, Yicheng; Li, Pinhua [Chinese Chemical Letters, 2021, vol. 32, # 12, p. 4033 - 4037]
[2]Niu, Kaikai; Hao, Yanke; Song, Lingyun; Liu, Yuxiu; Wang, Qingmin [Green Chemistry, 2021, vol. 23, # 1, p. 302 - 306]

81
[ 4441-56-9 ]
1-methyl-6-(trifluoromethyl)quinoxalin-2(1H)-one [ No CAS ]
1-cyclohexyl-1-methyl-6-(trifluoromethyl)-quinoxalin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With air In N,N-dimethyl-formamide at 20℃; for 12h; Irradiation;	2.1 Typical experimental procedure for the synthesis of 3-alkylquinoxalin-2(1H)-ones (3a-3ab) General procedure: A 10 mL oven-dried reaction vessel equipped with a magnetic stirrer was charged with quinoxalin-2(1H)-one (1, 0.20 mmol), alkylboronic acid (2, 0.40 mmol) and N,N-dimethylformamide (DMF, 2.0 mL). The reaction vessel was exposed to blue LED (440-445 nm, 1.5 W) irradiation at room temperature in air with stirring for 12 h. After completion of the reaction, the mixture was diluted with water and extracted with ethyl acetate, the organic layer was combined, dried over by anhydrous Na 2 SO 4 , and filtered, then concentrated to yield the crude product, which was further purified by flash chromatography (silica gel, petroleum ether/ethyl acetate = 10:1) to give the desired product 3a-3ad.
73%	With tert-butylammonium hexafluorophosphate(V); trifluoroacetic acid In N,N-dimethyl-formamide at 80℃; for 8h; Electrolysis;

Reference： [1]Yao, Lingling; Zhu, Defeng; Wang, Lei; Liu, Jie; Zhang, Yicheng; Li, Pinhua [Chinese Chemical Letters, 2021, vol. 32, # 12, p. 4033 - 4037]
[2]Niu, Kaikai; Hao, Yanke; Song, Lingyun; Liu, Yuxiu; Wang, Qingmin [Green Chemistry, 2021, vol. 23, # 1, p. 302 - 306]

82
[ 4441-56-9 ]
[ 1448363-20-9 ]
1-cyclohexyl-1-methyl-2-oxo-1,2-dihydroquinoxaline-6-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With air In N,N-dimethyl-formamide at 20℃; for 12h; Irradiation;	2.1 Typical experimental procedure for the synthesis of 3-alkylquinoxalin-2(1H)-ones (3a-3ab) General procedure: A 10 mL oven-dried reaction vessel equipped with a magnetic stirrer was charged with quinoxalin-2(1H)-one (1, 0.20 mmol), alkylboronic acid (2, 0.40 mmol) and N,N-dimethylformamide (DMF, 2.0 mL). The reaction vessel was exposed to blue LED (440-445 nm, 1.5 W) irradiation at room temperature in air with stirring for 12 h. After completion of the reaction, the mixture was diluted with water and extracted with ethyl acetate, the organic layer was combined, dried over by anhydrous Na 2 SO 4 , and filtered, then concentrated to yield the crude product, which was further purified by flash chromatography (silica gel, petroleum ether/ethyl acetate = 10:1) to give the desired product 3a-3ad.
65%	With tert-butylammonium hexafluorophosphate(V); trifluoroacetic acid In N,N-dimethyl-formamide at 80℃; for 8h; Electrolysis;

Reference： [1]Yao, Lingling; Zhu, Defeng; Wang, Lei; Liu, Jie; Zhang, Yicheng; Li, Pinhua [Chinese Chemical Letters, 2021, vol. 32, # 12, p. 4033 - 4037]
[2]Niu, Kaikai; Hao, Yanke; Song, Lingyun; Liu, Yuxiu; Wang, Qingmin [Green Chemistry, 2021, vol. 23, # 1, p. 302 - 306]

83
[ 4441-56-9 ]
6-methoxy-1-methylquinoxaline-2(1Η)-one [ No CAS ]
1-cyclohexyl-6-methoxy-1-methylquinoxalin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With air In N,N-dimethyl-formamide at 20℃; for 12h; Irradiation;	2.1 Typical experimental procedure for the synthesis of 3-alkylquinoxalin-2(1H)-ones (3a-3ab) General procedure: A 10 mL oven-dried reaction vessel equipped with a magnetic stirrer was charged with quinoxalin-2(1H)-one (1, 0.20 mmol), alkylboronic acid (2, 0.40 mmol) and N,N-dimethylformamide (DMF, 2.0 mL). The reaction vessel was exposed to blue LED (440-445 nm, 1.5 W) irradiation at room temperature in air with stirring for 12 h. After completion of the reaction, the mixture was diluted with water and extracted with ethyl acetate, the organic layer was combined, dried over by anhydrous Na 2 SO 4 , and filtered, then concentrated to yield the crude product, which was further purified by flash chromatography (silica gel, petroleum ether/ethyl acetate = 10:1) to give the desired product 3a-3ad.
82%	With tert-butylammonium hexafluorophosphate(V); trifluoroacetic acid In N,N-dimethyl-formamide at 80℃; for 8h; Electrolysis;

Reference： [1]Yao, Lingling; Zhu, Defeng; Wang, Lei; Liu, Jie; Zhang, Yicheng; Li, Pinhua [Chinese Chemical Letters, 2021, vol. 32, # 12, p. 4033 - 4037]
[2]Niu, Kaikai; Hao, Yanke; Song, Lingyun; Liu, Yuxiu; Wang, Qingmin [Green Chemistry, 2021, vol. 23, # 1, p. 302 - 306]

84
[ 82019-34-9 ]
[ 4441-56-9 ]
1-cyclohexyl-1,6,7-trimethylquinoxalin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With tert-butylammonium hexafluorophosphate(V); trifluoroacetic acid In N,N-dimethyl-formamide at 80℃; for 8h; Electrolysis;
80%	With air In N,N-dimethyl-formamide at 20℃; for 12h; Irradiation;	2.1 Typical experimental procedure for the synthesis of 3-alkylquinoxalin-2(1H)-ones (3a-3ab) General procedure: A 10 mL oven-dried reaction vessel equipped with a magnetic stirrer was charged with quinoxalin-2(1H)-one (1, 0.20 mmol), alkylboronic acid (2, 0.40 mmol) and N,N-dimethylformamide (DMF, 2.0 mL). The reaction vessel was exposed to blue LED (440-445 nm, 1.5 W) irradiation at room temperature in air with stirring for 12 h. After completion of the reaction, the mixture was diluted with water and extracted with ethyl acetate, the organic layer was combined, dried over by anhydrous Na 2 SO 4 , and filtered, then concentrated to yield the crude product, which was further purified by flash chromatography (silica gel, petroleum ether/ethyl acetate = 10:1) to give the desired product 3a-3ad.

Reference： [1]Niu, Kaikai; Hao, Yanke; Song, Lingyun; Liu, Yuxiu; Wang, Qingmin [Green Chemistry, 2021, vol. 23, # 1, p. 302 - 306]
[2]Yao, Lingling; Zhu, Defeng; Wang, Lei; Liu, Jie; Zhang, Yicheng; Li, Pinhua [Chinese Chemical Letters, 2021, vol. 32, # 12, p. 4033 - 4037]

85
[ 4441-56-9 ]
6,7-dichloro-1-methylquinoxaline-2(1H)-one [ No CAS ]
6,7-dichloro-3-cyclohexyl-1-methylquinoxalin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With air In N,N-dimethyl-formamide at 20℃; for 12h; Irradiation;	2.1 Typical experimental procedure for the synthesis of 3-alkylquinoxalin-2(1H)-ones (3a-3ab) General procedure: A 10 mL oven-dried reaction vessel equipped with a magnetic stirrer was charged with quinoxalin-2(1H)-one (1, 0.20 mmol), alkylboronic acid (2, 0.40 mmol) and N,N-dimethylformamide (DMF, 2.0 mL). The reaction vessel was exposed to blue LED (440-445 nm, 1.5 W) irradiation at room temperature in air with stirring for 12 h. After completion of the reaction, the mixture was diluted with water and extracted with ethyl acetate, the organic layer was combined, dried over by anhydrous Na 2 SO 4 , and filtered, then concentrated to yield the crude product, which was further purified by flash chromatography (silica gel, petroleum ether/ethyl acetate = 10:1) to give the desired product 3a-3ad.
58%	With tert-butylammonium hexafluorophosphate(V); trifluoroacetic acid In N,N-dimethyl-formamide at 80℃; for 8h; Electrolysis;

Reference： [1]Yao, Lingling; Zhu, Defeng; Wang, Lei; Liu, Jie; Zhang, Yicheng; Li, Pinhua [Chinese Chemical Letters, 2021, vol. 32, # 12, p. 4033 - 4037]
[2]Niu, Kaikai; Hao, Yanke; Song, Lingyun; Liu, Yuxiu; Wang, Qingmin [Green Chemistry, 2021, vol. 23, # 1, p. 302 - 306]

86
[ 4441-56-9 ]
1-methyl-6,7-difluoroquinoxaline-2(1H)-one [ No CAS ]
1-cyclohexyl-6,7-difluoro-1-methylquinoxalin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With air In N,N-dimethyl-formamide at 20℃; for 12h; Irradiation;	2.1 Typical experimental procedure for the synthesis of 3-alkylquinoxalin-2(1H)-ones (3a-3ab) General procedure: A 10 mL oven-dried reaction vessel equipped with a magnetic stirrer was charged with quinoxalin-2(1H)-one (1, 0.20 mmol), alkylboronic acid (2, 0.40 mmol) and N,N-dimethylformamide (DMF, 2.0 mL). The reaction vessel was exposed to blue LED (440-445 nm, 1.5 W) irradiation at room temperature in air with stirring for 12 h. After completion of the reaction, the mixture was diluted with water and extracted with ethyl acetate, the organic layer was combined, dried over by anhydrous Na 2 SO 4 , and filtered, then concentrated to yield the crude product, which was further purified by flash chromatography (silica gel, petroleum ether/ethyl acetate = 10:1) to give the desired product 3a-3ad.
52%	With tert-butylammonium hexafluorophosphate(V); trifluoroacetic acid In N,N-dimethyl-formamide at 80℃; for 8h; Electrolysis;

Reference： [1]Yao, Lingling; Zhu, Defeng; Wang, Lei; Liu, Jie; Zhang, Yicheng; Li, Pinhua [Chinese Chemical Letters, 2021, vol. 32, # 12, p. 4033 - 4037]
[2]Niu, Kaikai; Hao, Yanke; Song, Lingyun; Liu, Yuxiu; Wang, Qingmin [Green Chemistry, 2021, vol. 23, # 1, p. 302 - 306]

87
[ 4441-56-9 ]
[ 353261-88-8 ]
1-allyl-3-cyclohexylquinoxalin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With air In N,N-dimethyl-formamide at 20℃; for 12h; Irradiation;	2.1 Typical experimental procedure for the synthesis of 3-alkylquinoxalin-2(1H)-ones (3a-3ab) General procedure: A 10 mL oven-dried reaction vessel equipped with a magnetic stirrer was charged with quinoxalin-2(1H)-one (1, 0.20 mmol), alkylboronic acid (2, 0.40 mmol) and N,N-dimethylformamide (DMF, 2.0 mL). The reaction vessel was exposed to blue LED (440-445 nm, 1.5 W) irradiation at room temperature in air with stirring for 12 h. After completion of the reaction, the mixture was diluted with water and extracted with ethyl acetate, the organic layer was combined, dried over by anhydrous Na 2 SO 4 , and filtered, then concentrated to yield the crude product, which was further purified by flash chromatography (silica gel, petroleum ether/ethyl acetate = 10:1) to give the desired product 3a-3ad.
52%	With tert-butylammonium hexafluorophosphate(V); trifluoroacetic acid In N,N-dimethyl-formamide at 80℃; for 8h; Electrolysis;

Reference： [1]Yao, Lingling; Zhu, Defeng; Wang, Lei; Liu, Jie; Zhang, Yicheng; Li, Pinhua [Chinese Chemical Letters, 2021, vol. 32, # 12, p. 4033 - 4037]
[2]Niu, Kaikai; Hao, Yanke; Song, Lingyun; Liu, Yuxiu; Wang, Qingmin [Green Chemistry, 2021, vol. 23, # 1, p. 302 - 306]

88
[ 4441-56-9 ]
1-(propan-2-yn-1-yl)quinoxaline-2(1Η)-one [ No CAS ]
2-cyclohexyl-1-(prop-2-yn-1-yl)quinoxalin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With air In N,N-dimethyl-formamide at 20℃; for 12h; Irradiation;	2.1 Typical experimental procedure for the synthesis of 3-alkylquinoxalin-2(1H)-ones (3a-3ab) General procedure: A 10 mL oven-dried reaction vessel equipped with a magnetic stirrer was charged with quinoxalin-2(1H)-one (1, 0.20 mmol), alkylboronic acid (2, 0.40 mmol) and N,N-dimethylformamide (DMF, 2.0 mL). The reaction vessel was exposed to blue LED (440-445 nm, 1.5 W) irradiation at room temperature in air with stirring for 12 h. After completion of the reaction, the mixture was diluted with water and extracted with ethyl acetate, the organic layer was combined, dried over by anhydrous Na 2 SO 4 , and filtered, then concentrated to yield the crude product, which was further purified by flash chromatography (silica gel, petroleum ether/ethyl acetate = 10:1) to give the desired product 3a-3ad.
42%	With tert-butylammonium hexafluorophosphate(V); trifluoroacetic acid In N,N-dimethyl-formamide at 80℃; for 8h; Electrolysis;

Reference： [1]Yao, Lingling; Zhu, Defeng; Wang, Lei; Liu, Jie; Zhang, Yicheng; Li, Pinhua [Chinese Chemical Letters, 2021, vol. 32, # 12, p. 4033 - 4037]
[2]Niu, Kaikai; Hao, Yanke; Song, Lingyun; Liu, Yuxiu; Wang, Qingmin [Green Chemistry, 2021, vol. 23, # 1, p. 302 - 306]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	4441-56-9	MDL No. :	MFCD01311824
Formula :	C₆H₁₃BO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XDRVAZAFNWDVOE-UHFFFAOYSA-N
M.W :	127.98	Pubchem ID :	199578
Synonyms :

Num. heavy atoms :	9
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	37.98
TPSA :	40.46 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.99 cm/s

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.54
Log Po/w (WLOGP) :	0.79
Log Po/w (MLOGP) :	0.21
Log Po/w (SILICOS-IT) :	-0.62
Consensus Log Po/w :	0.39

[ CAS No. 4441-56-9 ] {[proInfo.proName]}

Quality Control of [ 4441-56-9 ]

Related Doc. of [ 4441-56-9 ]

Product Details of [ 4441-56-9 ]

Calculated chemistry of [ 4441-56-9 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 4441-56-9 ]

Application In Synthesis of [ 4441-56-9 ]

[ 4441-56-9 ] Synthesis Path-Upstream 1~1

[ 4441-56-9 ] Synthesis Path-Downstream 1~88

Related Functional Groups of
[ 4441-56-9 ]

Organoboron

Aliphatic Cyclic Hydrocarbons

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Log S (ESOL) :	-1.54
Solubility :	3.71 mg/ml ; 0.029 mol/l
Class :	Very soluble
Log S (Ali) :	-2.0
Solubility :	1.28 mg/ml ; 0.01 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.17
Solubility :	86.9 mg/ml ; 0.679 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.18

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 4441-56-9 ] {[proInfo.proName]}

Quality Control of [ 4441-56-9 ]

Related Doc. of [ 4441-56-9 ]

Product Details of [ 4441-56-9 ]

Calculated chemistry of [ 4441-56-9 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 4441-56-9 ]

Application In Synthesis of [ 4441-56-9 ]

[ 4441-56-9 ] Synthesis Path-Upstream 1~1

[ 4441-56-9 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 4441-56-9 ]

Organoboron

Aliphatic Cyclic Hydrocarbons

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 4441-56-9 ]