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[ CAS No. 939-27-5 ] {[proInfo.proName]}

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Product Details of [ 939-27-5 ]

CAS No. :939-27-5 MDL No. :MFCD00004127
Formula : C12H12 Boiling Point : -
Linear Structure Formula :- InChI Key :RJTJVVYSTUQWNI-UHFFFAOYSA-N
M.W : 156.22 Pubchem ID :13652
Synonyms :

Safety of [ 939-27-5 ]

Signal Word:Danger Class:9
Precautionary Statements:P201-P264-P280-P301+P330+P331-P312 UN#:3082
Hazard Statements:H302-H361-H372-H410 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 939-27-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 939-27-5 ]

[ 939-27-5 ] Synthesis Path-Downstream   1~85

  • 2
  • [ 1127-76-0 ]
  • [ 939-27-5 ]
  • 3
  • [ 939-27-5 ]
  • [ 5409-32-5 ]
YieldReaction ConditionsOperation in experiment
40% With chromium(VI) oxide In acetic acid at 20 - 30℃;
With chromium(VI) oxide; water; acetic acid at 45 - 60℃;
With chromium(VI) oxide; acetic acid
With chromium(VI) oxide In acetic acid

  • 4
  • [ 939-27-5 ]
  • [ 827-54-3 ]
YieldReaction ConditionsOperation in experiment
59% With 2-chloroanthracene-9,10-dione; cobalt(II) diacetate tetrahydrate; butane-2,3-dione dioxime In 1,2-dichloro-ethane at 20 - 30℃; for 36h; Irradiation; Schlenk technique; Sealed tube; Inert atmosphere;
With basic copper-iron-nickel contacts at 550℃;
With chromium (III)-oxide-magnesium oxide at 600 - 700℃; unter vermindertem Druck;
With zinc aluminate at 600 - 700℃; unter vermindertem Druck;
(i) NBS, AIBN, CCl4, (ii) KOtBu; Multistep reaction;

  • 7
  • [ 93-08-3 ]
  • [ 939-27-5 ]
YieldReaction ConditionsOperation in experiment
99% With hydrogen In para-xylene at 80℃; for 24h; Glovebox; Sealed tube; chemoselective reaction;
98% With PMHS; iron(III) chloride hexahydrate In 1,2-dichloro-ethane at 120℃; for 1h; Microwave irradiation;
95% With phenylsilane; 1,3-bis(perfluorophenyl)-4,5-diphenyl-1,2,3-triazol-3-ium tetrakis(3,5-bis-(trifluoromethyl)phenyl)borate In dichloromethane at 40℃; for 2h; Inert atmosphere; Schlenk technique; Sealed tube;
91% With hydrogen In methanol at 180℃; for 18h; Sealed tube; Green chemistry; chemoselective reaction;
90% With sodium hypophosphite monohydrate; 5%-palladium/activated carbon; hypophosphorous acid In lithium hydroxide monohydrate at 100℃; General procedures for the ketone reduction in alkane 1-19b General procedure: Method B: in a round bottom flask, to a solution of ketone (1mmol) and Pd/C 5wt% (50% in water) (212mg, 0.1mmol, 10mol%) in CPME (1mL) was added a mixture of sodium hypophosphite monohydrate (3mmol), hypophosphorous acid 50% in water (1mmol) in water (2mL). The reaction mixture was heated at 100°C between 2 and 16h. Same treatment as Method A was performed. (0038) Method C: the same procedure was followed replacing the thermal activation by a sonochemical activation during 5h.
84% With selenium powder; carbon monoxide; lithium hydroxide monohydrate; 1,5-diazabicyclo[5.4.0]undeca-5-ene In tetrahydrofuran at 120℃; for 24h;
83% With triethylsilane; tetracarbonylbis(μ-chloro)dirhodium(I) In dichloromethane at 0 - 20℃; for 24h; Inert atmosphere;
With hydrogenchloride; zinc,6a mercury,6b; benzene weiteres Reagens: Methanol;
With hydrogenchloride; zinc,6a mercury,6b; toluene
With hydrogenchloride; zinc,6a mercury,6b; toluene weiteres Reagens: Aethanol;
With hydrogenchloride; zinc,6a mercury,6b; toluene weiteres Reagens: Eisessig;
With pumice stone; nickel; benzene at 200℃; Hydrogenolyse;
With hydrogenchloride; palladium on activated charcoal; isopropanol Hydrogenolyse;
With sodium hydroxide; hydrazine hydrate monohydrate; diethylene glycol
With hydrogen; nickel at 180℃;
55 % Chromat. With indium(III) trichloride; dimethylmonochlorosilane In dichloromethane at 25℃; for 1h;
100 % Chromat. With hydrogen In toluene at 90℃; for 1h;
Multi-step reaction with 2 steps 1: methanol / 60 °C / Inert atmosphere 2: potassium carbonate; methanol; hydrogen; palladium 10% on activated carbon / 24 h / 65 °C / 760.05 Torr
Multi-step reaction with 2 steps 1: boron trifluoride diethyl ether complex / neat liquid / 15 h / 0 - 20 °C 2: tris(pentafluorophenyl)borate; triethylsilane / chloroform-d1 / 20 °C
Multi-step reaction with 2 steps 1: boron trifluoride diethyl ether complex / neat liquid / 15 h / 0 - 20 °C 2: tris(pentafluorophenyl)borate; triethylsilane / chloroform-d1 / 20 °C
Multi-step reaction with 3 steps 1: lithium aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 2: tributylphosphine; diethylazodicarboxylate / toluene / 12 h / 0 °C 3: tris(pentafluorophenyl)borate; triethylsilane / chloroform-d1 / 0.5 h / 20 °C
Multi-step reaction with 3 steps 1: lithium aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 2: tributylphosphine; diethylazodicarboxylate / toluene / 12 h / 0 °C 3: tris(pentafluorophenyl)borate; triethylsilane / chloroform-d1 / 1 h / 20 °C
Multi-step reaction with 3 steps 1: lithium aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 2: tributylphosphine; diethylazodicarboxylate / toluene / 12 h / 0 °C 3: tris(pentafluorophenyl)borate; triethylsilane / chloroform-d1 / 1 h / 20 °C
Multi-step reaction with 2 steps 1: sodium tetrahydridoborate / methanol / 20 °C 2: palladium (II) 2,4-pentanedionate; α,α'-bis(di-t-butylphosphino)-o-xylene; methanesulfonic acid; formic acid; 1,2-bis((di-tert-butylphosphoryl)methyl)benzene / 1,2-dichloro-ethane / 18 h / 100 °C / Schlenk technique; Sealed tube; Inert atmosphere
Multi-step reaction with 2 steps 1.1: boron trifluoride diethyl ether complex / dichloromethane / 20 °C / Inert atmosphere 2.1: sodium iodide; chloro-trimethyl-silane / dichloromethane / 40 h / 35 °C / Inert atmosphere; Green chemistry 2.2: 20 °C / Inert atmosphere; Green chemistry
With hydrogen In 1,3,5-trimethyl-benzene at 175℃; for 16h;

Reference: [1]Antil, Neha; Kumar, Ajay; Akhtar, Naved; Newar, Rajashree; Begum, Wahida; Manna, Kuntal [Inorganic Chemistry, 2021, vol. 60, # 12, p. 9029 - 9039]
[2]Location in patent: scheme or table Dal Zotto, Christophe; Virieux, David; Campagne, Jean-Marc [Synlett, 2009, # 2, p. 276 - 278]
[3]Avigdori, Idan; Fridman, Natalia; Gandelman, Mark; Koronatov, Aleksandr; Ranolia, Deepak; Singh, Kuldeep [Organic Letters, 2022]
[4]Petitjean, Laurene; Gagne, Raphael; Beach, Evan S.; Xiao, Dequan; Anastas, Paul T. [Green Chemistry, 2016, vol. 18, # 1, p. 150 - 156]
[5]Guyon, Carole; Baron, Marc; Lemaire, Marc; Popowycz, Florence; Métay, Estelle [Tetrahedron, 2014, vol. 70, # 12, p. 2088 - 2095]
[6]Nishiyama, Yutaka; Hamanaka, Sawako [Journal of Organic Chemistry, 1988, vol. 53, # 6, p. 1326 - 1329]
[7]Argouarch, Gilles [New Journal of Chemistry, 2019, vol. 43, # 28, p. 11041 - 11044]
[8]Fieser et al. [Journal of the American Chemical Society, 1939, vol. 61, p. 3216,3220] Buu-Hoi; Cagniant [Revue Scientifique, 1942, vol. 80, p. 271,273]
[9]Martin [Journal of the American Chemical Society, 1936, vol. 58, p. 1438,1439][Org. Reactions, 1942, vol. 1, p. 155,167]
[10]Sah [Recueil des Travaux Chimiques des Pays-Bas, 1940, vol. 59, p. 1029,1034]
[11]Bachmann; Cronyn; Struve [Journal of Organic Chemistry, 1947, vol. 12, p. 596,600]
[12]Levy [Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1931, vol. 192, p. 1397][Annales de Chimie (Cachan, France), 1938, vol. <11> 9, p. 5,39]
[13]Koelbel [Brennstoff-Chemie, 1949, vol. 30, p. 73,75]
[14]Belcher et al. [Journal of the Chemical Society, 1958, p. 3243,3246]
[15]Darzens; Rost [Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1908, vol. 146, p. 934]
[16]Miyai, Takashi; Ueba, Masako; Baba, Akio [Synlett, 1999, # 2, p. 182 - 184]
[17]Zaccheria, Federica; Ravasio, Nicoletta; Ercoli, Mauro; Allegrini, Pietro [Tetrahedron Letters, 2005, vol. 46, # 45, p. 7743 - 7745]
[18]Zhou, Lei; Liu, Zhenxing; Liu, Yizhou; Zhang, Yan; Wang, Jianbo [Tetrahedron, 2013, vol. 69, # 30, p. 6083 - 6087]
[19]Saito, Kodai; Kondo, Kazumi; Akiyama, Takahiko [Organic Letters, 2015, vol. 17, # 13, p. 3366 - 3369]
[20]Saito, Kodai; Kondo, Kazumi; Akiyama, Takahiko [Organic Letters, 2015, vol. 17, # 13, p. 3366 - 3369]
[21]Saito, Kodai; Kondo, Kazumi; Akiyama, Takahiko [Organic Letters, 2015, vol. 17, # 13, p. 3366 - 3369]
[22]Saito, Kodai; Kondo, Kazumi; Akiyama, Takahiko [Organic Letters, 2015, vol. 17, # 13, p. 3366 - 3369]
[23]Saito, Kodai; Kondo, Kazumi; Akiyama, Takahiko [Organic Letters, 2015, vol. 17, # 13, p. 3366 - 3369]
[24]Ciszek, Benjamin; Fleischer, Ivana [Chemistry - A European Journal, 2018, vol. 24, # 47, p. 12259 - 12263]
[25]Zhao, Guangkuan; Yuan, Ling-Zhi; Alami, Mouad; Provot, Olivier [Advanced Synthesis and Catalysis, 2018, vol. 360, # 13, p. 2522 - 2536]
[26]Offner-Marko, Lisa; Bordet, Alexis; Moos, Gilles; Tricard, Simon; Rengshausen, Simon; Chaudret, Bruno; Luska, Kylie L.; Leitner, Walter [Angewandte Chemie - International Edition, 2018, vol. 57, # 39, p. 12721 - 12726][Angew. Chem., 2018, vol. 130, # 39, p. 12903 - 12908,6]
  • 8
  • [ 917-64-6 ]
  • [ 139277-90-0 ]
  • [ 939-27-5 ]
YieldReaction ConditionsOperation in experiment
85% In benzene at 46℃; for 18h;
  • 9
  • [ 17743-32-7 ]
  • [ 557-20-0 ]
  • [ 939-27-5 ]
YieldReaction ConditionsOperation in experiment
74% With diisobutylaluminium hydride In tetrahydrofuran; hexane; toluene for 1.2h;
73 % Chromat. In tetrahydrofuran; hexane; toluene for 1.2h; Heating;
  • 10
  • [ 939-27-5 ]
  • [ 120342-65-6 ]
YieldReaction ConditionsOperation in experiment
38% With sodium azide; lithium perchlorate In acetic acid; acetonitrile at 25℃; for 10h; Inert atmosphere; Electrochemical reaction;
With tris-(2-chloro-ethyl)-amine; 2,3-dicyano-5,6-dichloro-p-benzoquinone In chloroform for 144h; Ambient temperature; Yield given;
  • 11
  • [ 939-27-5 ]
  • [ 27544-18-9 ]
  • [ 52193-85-8 ]
  • [ 93-08-3 ]
YieldReaction ConditionsOperation in experiment
With iodosylbenzene In dichloromethane at 0℃; for 1h; Yield given. Yields of byproduct given;
With 2,6-dichloropyridine N-oxide In benzene at 20℃; for 12h;
With 2,6-dichloropyridine N-oxide In benzene at 20℃; for 20h; Title compound not separated from byproducts;
  • 12
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YieldReaction ConditionsOperation in experiment
100% With C28H18Co(1-)*K(1+)*2C4H10O2; hydrogen In toluene at 20℃; for 3h; chemoselective reaction;
100% With iron(III) chloride; lithium aluminium tetrahydride; hydrogen In tetrahydrofuran at 18℃; for 6h; Inert atmosphere; Sealed tube;
99% With 2C2H3O2(1-)*Pd(2+)*3Na(1+)*C18H12O9PS3(3-); hydrogen; glycerol at 100℃; for 2h; Schlenk technique;
99% With hydrogen In tetrahydrofuran; ethanol at 25℃; Flow reactor; chemoselective reaction;
99% With hydrazine hydrate In tetrahydrofuran at 20℃; for 18h; Irradiation;
96% With hydrogen In benzene at 20℃; for 4h;
96% With Pd/C; C24H16N2O4 In ethanol at 50℃; for 18h; Glovebox;
93% With alpha-D-glucopyranose; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; sodium acetate In 1,2-dichloro-ethane at 120℃; for 24h; chemoselective reaction;
92% With hydrogen In ethanol at 20℃; for 2.5h; chemoselective reaction; 2.6. General procedure for the hydrogenation of different unsaturated compounds General procedure: In a typical reaction, 0.015 g of catalyst and 2 mmol of the reactant were taken in 10 mL of ethanol under hydrogen atmosphere. The reaction was monitored by thin-layer chromatography (TLC). After complete disappearance of the starting material, the catalyst was separated by simple filtration and the solvent was removed under reduced pressure to obtain the pure product.
91% With iron(III) chloride; lithium aluminium tetrahydride; hydrogen In tetrahydrofuran at 23℃; for 24h;
87% With dimethylamine borane; Rh/Al2O3 In toluene for 48h; Inert atmosphere;
84% With hydrogen; magnesium; 1,2-bis(2,6-diisopropylphenylimino)ethane; cobalt(II) bromide In tetrahydrofuran at 20℃; for 24h;
82% With tetra-(n-butyl)ammonium iodide; dimethyl amine; palladium dichloride In acetonitrile at 60℃; for 2.5h; Electrochemical reaction; Pd-catalyzed hydrogenation of alkenes to alkanes via electro-reduction Electro-reduction reaction was performed in three-necked round-bottomed flask (10 mL), with a graphite rod anode and a platinum disc cathode. 2 (0.80 mmol), PdCl2 (0.5 mol%, 0.7 mg), Me2NH (1.0 equiv, 0.4 mL, 2.0 M in the methonal), "nBu4NI (2.0 equiv, 291 mg) and MeCN (8.0 mL) were placed in a three-necked round-bottomed flask at 60 °C with a constant current of 0.3 Amaintained for 2.5-10 h. The mixture was cooled to room temperature, and diluted with 20 mL of EtOAc. The organic mixture was then washed with brine, dried over anh. Na2S04, and evaporated under vacuum. The residue was purified by flash column chromatography (n-hexane) on silica gel to provide the desired products 3g-3k.
65% With formic acid; tri-tert-butyl phosphine In tetrahydrofuran at 20℃; for 12h;
65% With formic acid; tri-tert-butyl phosphine In tetrahydrofuran at 20 - 60℃; for 12h;
36% With (1,2-dimethoxyethane)dichloronickel(II); para-iodoanisole; sodium t-butanolate In ethanol; benzene at 25℃; for 15h;
33% With 1-Methylpyrrolidine; C11H6MnNO6; hydrogen In tetrahydrofuran at 100℃; for 16h;
With hydridotetracarbonylcobalt; carbon monoxide In dichloromethane at 0℃;
With carbon dioxide; hydrogen at 36℃; for 1.5h;
With hydrogen at 55℃; for 24h;
97 %Spectr. With dimethylamine borane; ReBr2(NO)(CH3CN)(PTA)2 In ethanol at 70℃; for 23h; Inert atmosphere; 4.3. General procedure for the transfer hydrogenation of various terminal olefins according to Tables 2 and 3 General procedure: A solution of the proper olefin substrates (0.5 mmol), dimethylamine-borane (0.25 mmol) and 1 mol% of the rhenium complex (with 10-15 mol% of tBuOK according to Table 3) in the given solvent (0.8e1.0 ml) was stirred for given time at 70 °C under nitrogen atmosphere. Upon completion, the reaction mixture was filtered over Celite. The resulting solution was analyzed by 1H NMR spectroscopy. The obtained 1H NMR data of the alkanes were identical to those of the literature [35,49-55]. The yields are listed in Tables 2 and 3.
With ammonium hydroxide; hydrazine hydrate In ethanol at 60℃; for 4h;
With hydrazine hydrate In ethanol at 80℃; for 18h; Sealed tube; Sonication;
76 %Chromat. With hydrazine hydrate In chloroform at 25℃; for 24h;
With hydrogen In ethanol at 25℃; for 2h;
With hydrogen In ethanol at 25℃; for 0.333333h; Autoclave;
99 %Chromat. With hydrogen In glycerol at 80℃; for 2h;
78 mg With palladium 10% on activated carbon; hydrogen at 20℃; for 18h; Sealed tube;
With formic acid; ammonium formate In ethanol at 30℃; for 2h; Green chemistry;
With hydrogen In ethanol at 25℃; for 0.5h; Autoclave;
With palladium 10% on activated carbon; hydrogen In tert-Amyl alcohol at 100℃; for 24h;
99 %Chromat. With C34H44Br2Ir2N6; isopropyl alcohol; sodium t-butanolate for 24h; Inert atmosphere; Glovebox; Schlenk technique; Reflux;
With hydrogen In ethanol at 25℃;
With palladium 10% on activated carbon; hydrogen In tert-Amyl alcohol at 120℃;
43 %Chromat. With hydrogen In methanol at 40℃; for 20h; Autoclave;
97 %Spectr. With hydrogen In methanol at 25 - 27℃; for 16h; Autoclave;
With hydrogen; palladium diacetate In toluene at 110℃;
82 %Spectr. With chromium dichloride; hydrogen; magnesium; 1,2-bis(2,6-diisopropylphenylimino)ethane In tetrahydrofuran at 20℃; for 24h; Autoclave; regioselective reaction; 29 Example 29 Magnesium chips (10 mg, 0.4 mmol), CrCl2 (3.0 mg, 0.02 mmol) were sequentially added to a 25 mL reaction tube dried by an electric heat gun, after drying for about 5 minutes with an electric heat gun at 400 °C, cool to room temperature, transfer the reaction tube to a glove box, and add 2,6-diisopropylbenzene in bisimine (8 mg, 0.02 mmol) in turn, after 2-vinylnaphthalene (0.2 mmol), the reaction tube was removed from the glove box and 2 mL of freshly distilled tetrahydrofuran solvent was added under nitrogen. Set the temperature to 60 °C, and after the reaction for about 1 hour, the reaction solution becomes dark black, after cooling, the reaction system was quickly transferred to an autoclave, and the hydrogen was replaced three times. The hydrogen pressure was set to 2.0 MPa, and the reaction was carried out at room temperature for 24 h. After the reaction, 4 ml of saturated NH4Cl aqueous solution was added to the reaction tube, extracted three times with 10 ml of ethyl acetate, and the organic phases were combined. Add anhydrous sodium sulfate to dry, remove the solvent by vacuum distillation, the product was separated by silica gel column chromatography, use eluent (petroleum ether) for elution, 8a was obtained as a colorless oil in 82% yield.
With hydrazine hydrate; aluminium oxide nanoparticles In ethanol at 20℃; for 9h; Sealed tube; regioselective reaction; Reaction procedure General procedure: A 20 mL slunk tube was charged with 30 mg of nano-Al2O3, followed by 1 mmol of styrene and 1 mL of ethanol in a standard reaction process. 2 mmol of hydrazine hydrate was added gradually to this slurry. The reactor was then sealed with a Teflon screw cover, and the reaction mixture was stirred for the 9-h period given in Table 1. GC was used to track the development of the reaction by sampling aliquots at various time intervals. Following completion of the reaction, the reactor was cooled to room temperature, and the reaction mixture was diluted with ethanol and filtered. The product was then subjected to GC analysis to determine conversion and selectivity. The obtained products were confirmed by the GC-MS technique. The above-mentioned experimental protocol was repeated for the reusability test, with the exception that the solid extracted after the reaction was washed twice with ACN and dried at 80 °C for three hours. This dried solid was utilized in subsequent cycles with a new substrate.

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[30]Chen, Zhe; Wang, Weixue; Zhang, Yifei; Liang, Yu; Cui, Zhimin; Wang, Xiangke [Langmuir, 2018, vol. 34, # 43, p. 12809 - 12814]
[31]Guo, Bin; Yu, Tian-Qi; Li, Hong-Xi; Zhang, Shi-Qi; Braunstein, Pierre; Young, David J.; Li, Hai-Yan; Lang, Jian-Ping [ChemCatChem, 2019, vol. 11, # 10, p. 2500 - 2510]
[32]Donthireddy, S. N. R.; Illam, Praseetha Mathoor; Rit, Arnab; Singh, Vivek Kumar [Dalton Transactions, 2020, vol. 49, # 34, p. 11958 - 11970]
[33]Dong, Chao; Liu, Jian; Su, Panpan; Wang, Guang-Hui; Ye, Run-Ping; Yu, Qun [Angewandte Chemie - International Edition, 2020, vol. 59, # 42, p. 18374 - 18379][Angewandte Chemie, 2020, vol. 132, # 42, p. 18532 - 18537,6]
[34]Zhang, Shi-Qi; Cui, Yao; Guo, Bin; Young, David J.; Xu, Ze; Li, Hong-Xi [Tetrahedron, 2021, vol. 78]
[35]Klarner, Mara; Bieger, Sandra; Drechsler, Markus; Kempe, Rhett [Zeitschrift fur Anorganische und Allgemeine Chemie, 2021, vol. 647, # 22, p. 2157 - 2161]
[36]Beller, Matthias; Feng, Lu; Gao, Jie; Jackstell, Ralf; Jagadeesh, Rajenahally V.; Liu, Yuefeng; Ma, Rui [Angewandte Chemie - International Edition, 2021, vol. 60, # 34, p. 18591 - 18598][Angew. Chem., 2021, vol. 133, p. 18739 - 18746]
[37]Han, Zhangang; Hao, Zhiqiang; Lin, Jin; Lu, Guo-Liang; Zhang, Junhua; Zhang, Xiaoying [Organometallics, 2021, vol. 40, # 22, p. 3843 - 3853]
[38]Current Patent Assignee: YANAN UNIVERSITY - CN113860984, 2021, A Location in patent: Paragraph 0020
[39]Kaleeswari, Kalairajan; Tamil Selvi, Arunachalam [Research on Chemical Intermediates, 2022, vol. 48, # 4, p. 1495 - 1513]
  • 13
  • [ 64363-88-8 ]
  • [ 292638-84-7 ]
  • [ 91-20-3 ]
  • [ 694-87-1 ]
  • [ 939-27-5 ]
  • [ 827-54-3 ]
  • [ 91-57-6 ]
  • 14
  • [ 77341-12-9 ]
  • [ 292638-84-7 ]
  • [ 91-20-3 ]
  • [ 694-87-1 ]
  • [ 939-27-5 ]
  • [ 90-12-0 ]
  • [ 91-57-6 ]
  • 15
  • [ 557-20-0 ]
  • [ 132636-62-5 ]
  • [ 939-27-5 ]
YieldReaction ConditionsOperation in experiment
59% With diisobutylaluminium hydride; triphenylphosphine In 1,4-dioxane for 3h;
59% With triphenylphosphine In 1,4-dioxane; hexane; toluene for 3h; Heating;
  • 16
  • [ 939-27-5 ]
  • [ 79-04-9 ]
  • [ 75806-20-1 ]
  • [ 75806-21-2 ]
YieldReaction ConditionsOperation in experiment
1: 14% 2: 19% With aluminium trichloride In nitrobenzene Ambient temperature;
With hydrogenchloride In nitrobenzene 2 Preparation 2 Preparation 2 Chloroacetyl chloride (15.9 ml) is added to a mixture of 26.67 g of anhydrous aluminum chloride in 35 ml of nitrobenzene at 0° followedby the dropwise addition with stirring of 31.25 g of 2-ethylnaphthalene over 15 minutes. After stirring overnight at room temperature the mixture is poured on to a mixture of 500 g of ice and 100 ml concentrated hydrochloric acid. This is then extracted with ethyl acetate, the extractswashed with aqueous potassium carbonate, dried (MgSO4) and evaporated.After distillation of the nitrobenzene, the mixture is distilled as a yellow oil at 177° (0.4 mm). The resulting mixture of isomers is chromatographed on silica gel eluding with toluene to give 8.75 g of pure 1-chloroacetyl-7-ethylnaphthalene as an oil; and 6.3 g of 2-chloroacetyl-6-ethylnaphthalene as a colorless solid, recrystallized from hexane with mp 75°-76.5° C.
  • 17
  • [ 939-27-5 ]
  • [ 52428-02-1 ]
YieldReaction ConditionsOperation in experiment
97% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane at 70℃; for 3h;
With N-Bromosuccinimide
With carbon tetrabromide; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate In dichloromethane at 20℃; for 36h; Schlenk technique; Inert atmosphere; Irradiation; General experimental procedure: General procedure: To a 25 mL Schlenk tube was charged with ethylbenzene (0.5 mmol), tetrabromomethane (0.75 mmol), Ir(dtb-bpy)(ppy)2PF6 (4.6mg, 0.005 mmol, 1 mol %), and CH2Cl2 (2 mL). After being degassed by standardfrozen-thaw procedure, the reaction mixture were placed at a distance of 5 cm from a14 W compact fluorescent lamp and stirred at room temperature. After reaction completed, morpholine (20.0 equiv.) was added to the reaction mixture and stirredovernight. The reaction was quenched by water (5 mL), and extracted by ethyl acetate(3× 20mL). The combined organic layers were washed with brine and dried overanhydrous MgSO4. The mixture was filtered and the filtrate was concentrated underreduced pressure. The crude materials were purified by silica gel flashchromatography (PE/EtOAc) to give the desired products.
  • 18
  • [ 1485-07-0 ]
  • [ 5906-99-0 ]
  • [ 939-27-5 ]
  • 19
  • [ 939-27-5 ]
  • [ 93-08-3 ]
YieldReaction ConditionsOperation in experiment
91% With tert.-butylhydroperoxide; C45H52CuN4O3 In decane; acetonitrile at 70℃; for 36h; Reflux;
89% With tert.-butylhydroperoxide; [(pymox-Me2)2RuCl2]+BF4- In lithium hydroxide monohydrate at 20℃; for 16h;
85% With Caswell No. 744A; [bis(acetoxy)iodo]benzene; lithium hydroxide monohydrate In acetonitrile at 20℃; for 0.416667h;
81% With pyridine; NHPI; tetra-n-butylammonium tetrafluoroborate; oxygen In 2,2,2-trifluoroethanol; acetonitrile at 25 - 30℃; Electrolysis; 2.2.1 Procedure for mono-oxidation General procedure: An undivided cell was equipped with a magnet stirrer, platinum plate electrode (1.0×1.0×0.3 cm3), as the working electrode and counter electrode. Substrate (0.5 mmol),nBu4NBF4 (0.5 mmol, 164.6 mg), N-hydroxyphthalimide (NHPI, 0.1 mmol, 16.3 mg), and pyridine (1.0 mmol, 82 μL)were added to MeCN/2,2,2-trifluoroethan-1-ol (TFE) (5:1,3 mL). The electrolysis was conducted in an undivided cell equipped with O2 balloon at a constant current of 5 mA at room temperature (25-30 °C). When the reaction was completed, the solvent was removed under reduced pressure and the remaining crude product was purified by column chromatography over silica gel (petroleum ether/ethyl acetate(PE/EA)=30:1-10:1) to afford the corresponding aromatic ketone product.
79% With hydrogenchloride In lithium hydroxide monohydrate; acetonitrile at 20℃; for 8h; Irradiation;
77% With tert.-butylhydroperoxide; C26H23ClN8ORu In lithium hydroxide monohydrate at 20℃; for 2h; Schlenk technique;
73% With cerium(III) trichloride In lithium hydroxide monohydrate at 25℃; for 24h; Irradiation; Green chemistry;
66% With tert.-butylhydroperoxide; oxygen In lithium hydroxide monohydrate at 100℃; for 9h; Autoclave; Sealed tube;
66% With tert.-butylhydroperoxide; oxygen In lithium hydroxide monohydrate at 90℃; for 9h; 36 Example 36 Preparation of 2-naphthoethyNone Into a 5mL reaction flask were sequentially added magnetron, 0.5mmol 1-ethylnaphthalene (78mg), 20mg Cat-700 and 0.1mmol (20mol%) tert-butyl hydroperoxide (60% aqueous solution), and then put into the reaction In the kettle, 0.2MPa oxygen was charged into the reaction kettle. The reaction was carried out at 90°C for 9h. After the reaction was completed, it was cooled to room temperature, and excess oxygen was slowly released. 3 mL of ethyl acetate was added to the reaction system, the catalyst was recovered by centrifugation, and the catalyst was washed with ethyl acetate (3×3 mL). The organic layers were combined and desolvated under reduced pressure, and the residue was treated by column chromatography (ethyl acetate/petroleum ether=1:5) to obtain 2-naphthoethyl ketone, yield 66% (56.1 mg); white solid
60% With tert.-butylhydroperoxide In decane; acetonitrile at 80℃; for 0.285h; Flow reactor; Green chemistry;
51% With iron (ΙΙΙ) nitrate nonahydrate; NHPI; oxygen In acetonitrile at 25℃; for 40h;
41% With tert.-butylhydroperoxide In lithium hydroxide monohydrate; acetonitrile at 50℃; for 15h; Electrolysis;
12% With 1-ethoxy-4-nitropyridinium tetrafluoroborate In acetonitrile for 12h; Irradiation;
With 2,6-dichloropyridine N-oxide In dichloromethane at 65℃; for 24h;
With tert.-butylhydroperoxide at 90℃; for 7h; Neat (no solvent);
With tert.-butylhydroperoxide In neat (no solvent) at 89.84℃; for 5h; 2.3 Catalytic activity tests General procedure: Typically, 50 mg of catalyst, 1 mmol of substrate, and 3 mmol of 70% t-BuOOH (Sigma Aldrich) were taken in a RB flask and constantly stirred at 363 K for 5 h under solvent-free conditions. Unless otherwise specified the above reaction conditions are applicable. The catalyst was separated by filtration and analyzed by GC (GC-17A model, M/s. Shimadzu Instruments, Japan) consisting of FID and OV-1 capillary column (0.53 mm × 30 m) using toluene as external standard. The product identification was made by GC-MS (QP5050 model, M/s. Shimadzu Instruments, Japan) consisting of DB-5 column (0.32 mm dia. and 25 m long, M/s. J & W Scientific, USA). The separated catalyst was washed with methanol and dried under vacuum prior to reuse.
With tert.-butylhydroperoxide In lithium hydroxide monohydrate at 80℃; for 12h; Green chemistry;
With tert.-butylhydroperoxide In ethylbenzene; lithium hydroxide monohydrate at 80℃; for 12h;
With NHPI; oxygen In acetonitrile at 60℃; for 14h;
With pyridine; tert.-butylhydroperoxide; iodine In lithium hydroxide monohydrate at 80℃; for 10h; Sealed tube;
With tert.-butylhydroperoxide In lithium hydroxide monohydrate at 80℃; for 12h; Sealed tube;
With tert.-butylhydroperoxide In lithium hydroxide monohydrate at 90℃; for 6h; Green chemistry; 2.7 Catalytic activity test for selective benzylic oxidation of tetralin in water medium General procedure: In a typical experiment, 50mg of Cu(II)/γ-Fe2O3SBA-15 catalyst was dispersed in 2mL of water in 10mL capacity round bottom flask fitted with a water condenser, which is open to air. Subsequently, 1mmol tetralin and 3mmol of TBHP (70% in aqueous solution) were added and conducted the reaction at 90°C for 6h at constant stirring. After completion of the reaction, catalyst was removed from the product mixture by simple magnetic separation. Then, the product mixture is extracted with ethylacetate followed by drying over anhydrous MgSO4 to remove traces of water and the samples were analyzed by a gas chromatograph (GC-17A, M/s. Shimadzu Instruments, Japan) using an Equity-5 capillary column (0.53mm x 30m). The products were confirmed by GC-MS (QP-5050 model, M/s. Shimadzu Instruments, Japan) equipped with DB-5 capillary column (0.32mm dia. and 25m long, M/s. J & W Scientific, USA).
With ketoreductase-P3-B03; oxygen; NADPH; 9-mesityl-10-methylacridin-10-ium perchlorate In lithium hydroxide monohydrate; acetonitrile at 23℃; for 24h; Irradiation; Enzymatic reaction;
92 %Chromat. With oxygen; sodium trifluoro-methanesulfinate In acetonitrile at 25℃; for 12h; Irradiation; Green chemistry;
With oxygen In neat (no solvent) at -10.16℃; for 10h; Green chemistry;
With phosphoric acid; dihydrogen peroxide; tri-n-octylmethylammonium chloride; tungstic acid In toluene at 80℃; for 6h;
With tert.-butylhydroperoxide In lithium hydroxide monohydrate at 35℃; for 48h; regioselective reaction;
With tert.-butylhydroperoxide; 9C7H5O2(1-)*3Eu(3+) In ethanol at 60℃; for 4h;

Reference: [1]Location in patent: experimental part Wu, Xianghong; Gorden, Anne E. V. [European Journal of Organic Chemistry, 2009, # 4, p. 503 - 509]
[2]Yi, Chae S.; Kwon, Ki-Hyeok; Lee, Do W. [Organic Letters, 2009, vol. 11, # 7, p. 1567 - 1569]
[3]Location in patent: scheme or table Telvekar, Vikas N.; Sasane, Kulbhushan A. [Synthetic Communications, 2012, vol. 42, # 9, p. 1325 - 1329]
[4]Li, Zhibin; Zhang, Yan; Li, Kuiliang; Zhou, Zhenghong; Zha, Zhenggen; Wang, Zhiyong [Science China Chemistry, 2021, vol. 64, # 12, p. 2134 - 2141]
[5]Niu, Kaikai; Shi, Xiaodi; Ding, Ling; Liu, Yuxiu; Song, Hongjian; Wang, Qingmin [ChemSusChem, 2022, vol. 15, # 2]
[6]Bo, Chun-Bo; Bu, Qingqing; Li, Xue; Ma, Ge; Wei, Donghui; Guo, Cheng; Dai, Bin; Liu, Ning [Journal of Organic Chemistry, 2020, vol. 85, # 6, p. 4324 - 4334]
[7]Xie, Pan; Xue, Cheng; Shi, Sanshan; Du, Dongdong [ChemSusChem, 2021, vol. 14, # 13, p. 2689 - 2693]
[8]Ju, Zhao-Yang; Song, Li-Na; Chong, Ming-Ben; Cheng, Dang-Guo; Hou, Yang; Zhang, Xi-Ming; Zhang, Qing-Hua; Ren, Lan-Hui [Journal of Organic Chemistry, 2022, vol. 87, # 6, p. 3978 - 3988]
[9]Current Patent Assignee: ZHEJIANG UNIVERSITY - CN113816899, 2021, A Location in patent: Paragraph 0104-0105
[10]Pandey, Akanksha M.; Agalave, Sandip G.; Vinod, Chathakudath P.; Gnanaprakasam, Boopathy [Chemistry - An Asian Journal, 2019, vol. 14, # 19, p. 3414 - 3423]
[11]Miao, Chengxia; Zhao, Hanqing; Zhao, Quanyi; Xia, Chungu; Sun, Wei [Catalysis science and technology, 2016, vol. 6, # 5, p. 1378 - 1383]
[12]Marko, Jason A.; Durgham, Anthony; Bretz, Stacey Lowery; Liu, Wei [Chemical Communications, 2019, vol. 55, # 7, p. 937 - 940]
[13]Negele, Stephan; Wieser, Katja; Severin, Theodor [Journal of Organic Chemistry, 1998, vol. 63, # 4, p. 1138 - 1143]
[14]Zhang, Jun-Long; Huang, Jie-Sheng; Che, Chi-Ming [Chemistry - A European Journal, 2006, vol. 12, # 11, p. 3020 - 3031]
[15]Location in patent: scheme or table Anand, Narani; Reddy, Kannapu Hari Prasad; Prasad, Ganjala Venkata Siva; Rama Rao, Kamaraju Seetha; Burri, David Raju [Catalysis Communications, 2012, vol. 23, p. 5 - 9]
[16]Neeli, Chinna Krishna Prasad; Narani, Anand; Marella, Ravi Kumar; Rama Rao, Kamaraju Seetha; Burri, David Raju [Catalysis Communications, 2013, vol. 39, p. 5 - 9]
[17]Singh, Ajay K.; Basavaraju; Sharma, Siddharth; Jang, Seungwook; Park, Chan Pil; Kim, Dong-Pyo [Green Chemistry, 2014, vol. 16, # 6, p. 3024 - 3030]
[18]Yang, Shuliang; Peng, Li; Huang, Peipei; Wang, Xiaoshi; Sun, Yongbin; Cao, Changyan; Song, Weiguo [Angewandte Chemie - International Edition, 2016, vol. 55, # 12, p. 4016 - 4020][Angew. Chem., 2016, vol. 128, # 12, p. 4084 - 4088,5]
[19]Majumdar, Biju; Bhattacharya, Tamalika; Sarma, Tridib K. [ChemCatChem, 2016, vol. 8, # 10, p. 1825 - 1835]
[20]Ramanathan, Mani; Kuo, Chun-Kai; Liu, Shiuh-Tzung [Organic and Biomolecular Chemistry, 2016, vol. 14, # 48, p. 11446 - 11453]
[21]Zhu, Ya-Nan; Cao, Chang-Yan; Jiang, Wen-Jie; Yang, Shu-Liang; Hu, Jin-Song; Song, Wei-Guo; Wan, Li-Jun [Journal of Materials Chemistry A, 2016, vol. 4, # 47, p. 18470 - 18477]
[22]Neeli, Chinna Krishna Prasad; Kannapu, Hari Prasad Reddy; Kalevaru, Venkat Narayana; Kamaraju, Seetha Rama Rao; Burri, David Raju [Molecular catalysis, 2018, vol. 453, p. 74 - 84]
[23]Betori, Rick C.; May, Catherine M.; Scheidt, Karl A. [Angewandte Chemie - International Edition, 2019, vol. 58, # 46, p. 16490 - 16494][Angew. Chem., 2019, vol. 131, p. 16642 - 16646,5]
[24]Fu, Hua; Liu, Can; Liu, Yong; Yang, Haijun; Zhu, Xianjin [Green Chemistry, 2020, vol. 22, # 13, p. 4357 - 4363]
[25]Assiri, Mohammed A.; Bhaumik, Asim; Ha, Chang-Sik; Selvaraj, Manickam; Subrahmanyam, Ch. [Dalton Transactions, 2020, vol. 49, # 28, p. 9710 - 9718]
[26]Francisco, Manuel; Hutchings, Graham J.; Jenkins, Robert L.; Knight, David W.; Nowicka, Ewa; Sankar, Meenakshisundaram; Taylor, Stuart H.; Willock, David J. [New Journal of Chemistry, 2021, vol. 45, # 31, p. 13885 - 13892]
[27]Cheng, Yujie; Sun, Qingdi; Huang, Liyun; He, Qian; Zhang, Hao; Wang, Pengbo; Zhang, Ying; Shi, Shaolin; Zhang, Xingcong; Gan, Tao; He, Xiaohui; Ji, Hongbing [Dalton Transactions, 2021, vol. 50, # 34, p. 11711 - 11715]
[28]Zhang, Yin; Yu, Wei-Dong; Zhao, Cai-Feng; Yan, Jun [Chinese Journal of Chemistry, 2022, vol. 40, # 4, p. 480 - 486]
  • 20
  • polyethylene [ No CAS ]
  • [ 1127-76-0 ]
  • [ 939-27-5 ]
  • [ 827-54-3 ]
  • [ 643-58-3 ]
  • 21
  • [ 91-20-3 ]
  • [ 74-85-1 ]
  • silicon dioxide aluminium oxide [ No CAS ]
  • [ 1127-76-0 ]
  • [ 939-27-5 ]
  • 22
  • [ 1127-76-0 ]
  • silica gel [ No CAS ]
  • [ 939-27-5 ]
  • 23
  • [ 827-54-3 ]
  • [ 62-53-3 ]
  • [ 939-27-5 ]
  • [ 108079-37-4 ]
  • 2-(2-Naphthylmethyl)-3-(2-naphthyl)quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 29% 2: 12 % Chromat. With triphenylphosphine In toluene at 140℃; for 48h;
  • 24
  • [ 939-27-5 ]
  • [ 75-36-5 ]
  • [ 105523-17-9 ]
YieldReaction ConditionsOperation in experiment
86% In 1,2-dichloro-ethane at 20℃; for 18h;
86% With aluminum (III) chloride In 1,2-dichloro-ethane at 20℃; for 18h; 2 7-Ethyl-1-naphthoic Acid (24). 7-Ethyl-1-naphthoic Acid (24). To a mixture of 9.56 g of AlCl3(64 mmol) and 4.05 mL of acetyl chloride (57 mmol) was added, with stirring, 21.3 mL of 1,2-dichloroethane. To this light brown solution was added dropwise a solution of 10.0 g (64 mmol) of 2-ethylnaphthalene in 7.1 mL of 1,2-dichloroethane. The reaction mixture was allowed to stand at ambient temperature for 18 h, diluted with dichloromethane, and shaken with dilute aqueous HCl. After washing with saturated aqueous NaHCO3 and water, the organic phase was dried (MgSO4) and the solvents were removed in vacuo. Chromatography (petroleum ether:ethyl acetate, 95:5) gave 9.88 g (86%) of 1-acetyl-7-ethylnaphthalene (26) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 1.33 (t, J=7.6 Hz, 3H), 2.72 (s, 3H), 2.83 (q, J=7.5 Hz, 2H), 7.39-7.50 (m, 2H), 7.79 (d, J=8.4 Hz, 1H), 8.56 (s, 1H); 13C NMR (75.5 MHz, CDCl3) δ 15.5, 29.5, 30.0, 123.4, 123.8, 127.5, 128.3, 128.7, 130.3, 132.4, 132.7, 134.6, 144.3, 202.1.
  • 25
  • [ 91-20-3 ]
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YieldReaction ConditionsOperation in experiment
In n-heptane; water at 180℃; for 2h;
  • 26
  • [ 816444-61-8 ]
  • [ 939-27-5 ]
  • (1R)-[N-(p-toluenesulfonyl)-p-toluenesulfonimidoyl]-2-(1-aminoethyl)naphthalene [ No CAS ]
  • (1S)-[N-(p-toluenesulfonyl)-p-toluenesulfonimidoyl]-2-(1-aminoethyl)naphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With dirhodium(II) tetrakis[N-(1,8-naphthaloyl)-(S)-tert-leucinate]; 4 A molecular sieve; bis(tertbutylcarbonyloxy)iodobenzene In methanol; 1,1,2,2-tetrachloroethane at -35℃; for 72h;
  • 27
  • [ 93-08-3 ]
  • [ 939-27-5 ]
  • [ 7228-47-9 ]
YieldReaction ConditionsOperation in experiment
1: 86 % Spectr. 2: 9 % Spectr. With hydrogen In hexane at 20℃; for 36h;
With sodium hypophosphite monohydrate; 5%-palladium/activated carbon; hypophosphorous acid In water at 20℃; for 5h; Sonication; General procedures for the ketone reduction in alkane 1-19b General procedure: Method B: in a round bottom flask, to a solution of ketone (1mmol) and Pd/C 5wt% (50% in water) (212mg, 0.1mmol, 10mol%) in CPME (1mL) was added a mixture of sodium hypophosphite monohydrate (3mmol), hypophosphorous acid 50% in water (1mmol) in water (2mL). The reaction mixture was heated at 100°C between 2 and 16h. Same treatment as Method A was performed. (0038) Method C: the same procedure was followed replacing the thermal activation by a sonochemical activation during 5h.
  • 29
  • [ 573-98-8 ]
  • [ 569-41-5 ]
  • [ 91-20-3 ]
  • [ 581-40-8 ]
  • [ 582-16-1 ]
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  • [ 575-43-9 ]
  • [ 581-42-0 ]
  • [ 939-27-5 ]
  • [ 575-37-1 ]
  • [ 575-41-7 ]
  • [ 571-58-4 ]
  • [ 571-61-9 ]
  • [ 90-12-0 ]
  • [ 91-57-6 ]
YieldReaction ConditionsOperation in experiment
1.33%Chromat.; 2.56%Chromat.; 0.36%Chromat.; 1.43%Chromat.; 2.46%Chromat.; 1.56%Chromat.; 0.24%Chromat.; 1.05%Chromat.; 4.31%Chromat. With hydrogen;chromium corundum; at 20 - 500.6℃; under 59631 Torr;Purification / work up; Example 9 (Hydrodealkylation) A 70 g amount of Cr2O3/Al2O3 type catalyst produced by Sud-Chemie AG is charged into a tubular reactor. The reactor is heated gradually from ambient temperature to 932 F (500 C) to dry the catalyst while supplying hydrogen gas. Thereupon distillation product (Blend-B) obtained from Example 8 is supplied to the reactor at the rate of 70 g/hr and 1.0 hr-1 in WHSV, while supplying hydrogen gas at 0.98 scf/hr (0.028 m3/hr). The hydrodealkylation reaction is carried out at 933 F (500.6 C) and 1138 psig (7.95 MPa). The product is analyzed by GC and the results of hydrodealkylation are summarized in Table 8 below.
4.75%Chromat.; 3.76%Chromat.; 0.44%Chromat.; 2.17%Chromat.; 3.53%Chromat.; 2.13%Chromat.; 0.34%Chromat.; 2.44%Chromat.; 9.48%Chromat. With hydrogen;cobalt oxide and molybdenum oxide on alumina; at 20 - 500℃; under 74482.4 Torr; Example 10 (Hydrodealkylation) A 70 g amount of CoO/MoO3/Al2O3 type catalyst produced by Akzo Chemicals Inc. is charged into a tubular reactor. The reactor is heated gradually from ambient temperature to 300F (148.9 C) with nitrogen flow at 5 scf/hr (0.142 m3/hr). Then the flow gas is switched to hydrogen at 2 scf/hr (0.057 m3/hr) and pressure is increased to 500 psig (3.55 MPa). Catalyst is contacted with an organic sulfide (Kerosene with 1.0% of Dimethyldisulfide) for sulfiding while supplying hydrogen gas and then temperature is raised to 650 F (343.3 C). Thereupon distillation product (Blend-B) obtained from Example 8 is fed to the reactor at the rate of 70 g/hr and 1.0 hr-1 in WHSV, while supplying hydrogen gas at 5scf/hr (0.028 m3/hr). Hydrodealkylation is carried out at 932 F (500 C) and 425 psig (9.93 Mpa) The product is analyzed by GC and the results of hydrodealkylation are summarized in Table 8 below. As shown in Table 8, both Cr2O3/Al2O3, and CoO/MoO3/Al2O3 type catalyst are effective to enrich DMN isomers from DMN lean feed.
  • 30
  • [ 581-40-8 ]
  • [ 573-98-8 ]
  • [ 571-58-4 ]
  • [ 91-20-3 ]
  • [ 582-16-1 ]
  • [ 1127-76-0 ]
  • [ 575-43-9 ]
  • [ 581-42-0 ]
  • [ 939-27-5 ]
  • [ 575-37-1 ]
  • [ 575-41-7 ]
  • [ 569-41-5 ]
  • [ 571-61-9 ]
  • [ 90-12-0 ]
  • [ 91-57-6 ]
YieldReaction ConditionsOperation in experiment
3.11%Chromat.; 4.58%Chromat.; 0.26%Chromat.; 2.92%Chromat.; 4.86%Chromat.; 0.57%Chromat.; 0.12%Chromat.; 0.39%Chromat.; 3.71%Chromat.; 15.68%Chromat. With hydrogen;chromium corundum; at 20 - 475℃; under 44929.5 Torr;Conversion of starting material; Example 4 (Hydrodealkylation) A part of Fraction-17 and Residue shown in Table 3 are mixed to prepare the feedstock(Blend-A) for hydrodealkylation. A 50 g amount of Cr2O3/Al2O3 type catalyst produced by Sud-Chemie AG is charged into a tubular reactor. The reactor is heated gradually from ambient temperature to 662F (350 C) to dry the catalyst while supplying hydrogen gas. Thereupon Blend-A is fed to the reactor at the rate of 50 g/hr and 1.0 hr-1 in WHSV, while supplying hydrogen gas at 1.25 cf/hr (0.034 m3/hr). Hydrodealkylation is carried out at 887F (475 C) and 854 psig (5.99 MPa). The product is analyzed by GC and the results of hydrodealkylation are summarized in Table 4 below. As shown in Table 4, Cr2O3/Al2O3 type catalyst is effective to enrich 2,6-DMN from 2,6-DMN lean feed.
  • 31
  • [ 120-94-5 ]
  • [ 124-38-9 ]
  • [ 939-27-5 ]
  • (+-)-2-[2]naphthyl-propionic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With n-butyllithium In water 4 EXAMPLE 4 EXAMPLE 4 To a dried solvent of 1-methylpyrrolidine (80 ml.) were added potassium tertiary-butoxide (17.5 g., 156 mmoles), 6.40 ml. β-ethylnaphthalene (6.30 g., 40.4 mmoles) under a nitrogen atmosphere. After stirring for 15 minutes under ice-water cooling, n-butyllithium (2.50 M) (12.0 ml, 30.0 mmoles) was introduced dropwise over a period of about 10 minutes. A greenish blue color developed and the contents began jelling up. Additional 1-methylpyrrolidine (50 ml.) was added to help bring the jell back into solution. The reaction was continued for 5 hours at 0° C. The final color was bluish green. The reaction mixture was then transferred into a dry-box and carbonated with dry-ice (200 ml.) under a nitrogen atmosphere. On the next morning, the white solid mass was hydrolyzed with water (3 ml.). After the removal of the volatile materials under vacuum, the pasty material was dissolved in water, washed with hexane and extracted with ether (3 times). The combined ethereal extracts were dried over sodium sulfate, filtered and concentrated to afford the crude 2-(β-naphthyl)propionic acid crystals (3.43 g.).
  • 32
  • [ 939-27-5 ]
  • [ 7228-47-9 ]
  • [ 100518-70-5 ]
  • [ 93-08-3 ]
YieldReaction ConditionsOperation in experiment
With oxygen In dichloromethane at 20℃; for 4h; Irradiation;
  • 33
  • [ 939-27-5 ]
  • [ 41085-71-6 ]
  • 4-methyl-N-(α-(naphthalen-2-yl)ethyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% With 5A molecular sieve In acetonitrile at 20℃;
  • 34
  • [ 939-27-5 ]
  • [ 94892-50-9 ]
  • [ 816444-62-9 ]
  • (1R)-[N-(p-toluenesulfonyl)-p-toluenesulfonimidoyl]-2-(1-aminoethyl)naphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With 4 A molecular sieve In methanol; 1,1,2,2-tetrachloroethane at -35℃; for 72h;
  • 35
  • [ 1592-38-7 ]
  • [ 75-16-1 ]
  • [ 939-27-5 ]
YieldReaction ConditionsOperation in experiment
4% In diethyl ether; toluene at 25℃; for 15h;
  • 36
  • [ 42101-92-8 ]
  • [ 75-16-1 ]
  • [ 939-27-5 ]
YieldReaction ConditionsOperation in experiment
80% In diethyl ether; toluene at 25℃; for 15h;
  • 37
  • [ 939-27-5 ]
  • 2,2,2,-trichloroethoxycarbonyl azide [ No CAS ]
  • [ 1205060-70-3 ]
YieldReaction ConditionsOperation in experiment
92% With cobalt(II) 5,10,15,20-tetraphenylporphyrin at 40℃; for 48h; Molecular sieve; Inert atmosphere; Neat (no solvent);
  • 38
  • [ 22250-78-8 ]
  • [ 939-27-5 ]
YieldReaction ConditionsOperation in experiment
81% With chloro(1,5-cyclooctadiene)rhodium(I) dimer; chlorotriisopropylsilane In ethylcyclohexane at 130℃; for 15h; Inert atmosphere;
  • 39
  • [ 939-27-5 ]
  • [ 613-54-7 ]
YieldReaction ConditionsOperation in experiment
60% With hydrogen bromide; oxygen In water; ethyl acetate at 20℃; for 24h; Irradiation;
  • 40
  • [ 939-27-5 ]
  • [ 13651-05-3 ]
YieldReaction ConditionsOperation in experiment
41% With carbon tetrabromide; hydrogen bromide; oxygen In water; ethyl acetate at 40℃; Irradiation; A typical procedure is as follows: A EtOAc solution (5 mL) of ethylbenzene (0.3 mmol) and 48% aq HBr (0.75 mmol) in a pyrex test tube equipped with an O2 balloon was stirred and irradiated with four 22-W fluorescent lamps, which were placed at a distance of 65 mm, for 10 h. The temperature at the final stage of this reaction was approximately 40 °C. The reaction mixtures were concentrated under reduced pressure, and the pure products were obtained by preparative TLC.
  • 41
  • [ 7228-47-9 ]
  • [ 939-27-5 ]
YieldReaction ConditionsOperation in experiment
94% With formic acid; methanesulfonic acid; 1,2-bis((di-tert-butylphosphoryl)methyl)benzene; palladium (II) 2,4-pentanedionate; α,α'-bis(di-t-butylphosphino)-o-xylene In 1,2-dichloro-ethane at 100℃; for 18h; Schlenk technique; Sealed tube; Inert atmosphere;
92% With ferric(III) chloride In 1,2-dichloro-ethane at 20℃; for 1h; chemoselective reaction;
87.8% With hydrogen In ethanol at 120℃; for 8h; chemoselective reaction;
87.8% With hydrogen In ethanol at 120℃; for 8h; chemoselective reaction;
46% With iron(III) trifluoride; trifluorormethanesulfonic acid; 2-nitrobenzenesulfonyl hydrazide In nitromethane at 20℃; for 1h; Inert atmosphere; chemoselective reaction;
Multi-step reaction with 2 steps 1: tributylphosphine; diethylazodicarboxylate / toluene / 12 h / 0 °C 2: tris(pentafluorophenyl)borate; triethylsilane / chloroform-d1 / 0.5 h / 20 °C
Multi-step reaction with 2 steps 1: tributylphosphine; diethylazodicarboxylate / toluene / 12 h / 0 °C 2: tris(pentafluorophenyl)borate; triethylsilane / chloroform-d1 / 1 h / 20 °C
Multi-step reaction with 2 steps 1: tributylphosphine; diethylazodicarboxylate / toluene / 12 h / 0 °C 2: tris(pentafluorophenyl)borate; triethylsilane / chloroform-d1 / 1 h / 20 °C
Multi-step reaction with 2 steps 1: 4-dimethylaminopyridine / dichloromethane / 16 h / 0 - 20 °C / Schlenk technique; Inert atmosphere 2: triethylsilane; tris(pentafluorophenyl)borate / dichloromethane / 0.08 h / 20 °C / Schlenk technique; Inert atmosphere
Multi-step reaction with 2 steps 1: 1H-imidazole / dichloromethane / 2 h / 20 °C / Schlenk technique; Inert atmosphere 2: triethylsilane; tris(pentafluorophenyl)borate / dichloromethane / 0.08 h / 20 °C / Schlenk technique; Inert atmosphere
Multi-step reaction with 2 steps 1: triethylamine / 16 h / 20 °C / Schlenk technique; Inert atmosphere 2: triethylsilane; tris(pentafluorophenyl)borate / dichloromethane / 0.08 h / 20 °C / Schlenk technique; Inert atmosphere
Multi-step reaction with 2 steps 1: pyridine / 18 h / 100 °C / Schlenk technique; Inert atmosphere 2: triethylsilane; tris(pentafluorophenyl)borate / dichloromethane / 0.08 h / 20 °C / Schlenk technique; Inert atmosphere

Reference: [1]Ciszek, Benjamin; Fleischer, Ivana [Chemistry - A European Journal, 2018, vol. 24, # 47, p. 12259 - 12263]
[2]Location in patent: experimental part Chan, Li Yan; Lim, Jazreel Seh Kai; Kim, Sunggak [Synlett, 2011, # 19, p. 2862 - 2866]
[3]Xu, Caiyun; Wu, Haihong; Zhang, Zhanrong; Zheng, Bingxiao; Zhai, Jianxin; Zhang, Kaili; Wu, Wei; Mei, Xuelei; He, Mingyuan; Han, Buxing [Chemical Science, 2022, vol. 13, # 6, p. 1629 - 1635]
[4]Xu, Caiyun; Wu, Haihong; Zhang, Zhanrong; Zheng, Bingxiao; Zhai, Jianxin; Zhang, Kaili; Wu, Wei; Mei, Xuelei; He, Mingyuan; Han, Buxing [Chemical Science, 2022, vol. 13, # 6, p. 1629 - 1635]
[5]Yang, Zonglian; Kumar, Rapolu Kiran; Liao, Peiqiu; Liu, Zhaohong; Li, Xingqi; Bi, Xihe [Chemical Communications, 2016, vol. 52, # 35, p. 5936 - 5939]
[6]Saito, Kodai; Kondo, Kazumi; Akiyama, Takahiko [Organic Letters, 2015, vol. 17, # 13, p. 3366 - 3369]
[7]Saito, Kodai; Kondo, Kazumi; Akiyama, Takahiko [Organic Letters, 2015, vol. 17, # 13, p. 3366 - 3369]
[8]Saito, Kodai; Kondo, Kazumi; Akiyama, Takahiko [Organic Letters, 2015, vol. 17, # 13, p. 3366 - 3369]
[9]Oestreich, Martin; Richter, Sven C. [European Journal of Organic Chemistry, 2021, vol. 2021, # 14, p. 2103 - 2106]
[10]Oestreich, Martin; Richter, Sven C. [European Journal of Organic Chemistry, 2021, vol. 2021, # 14, p. 2103 - 2106]
[11]Oestreich, Martin; Richter, Sven C. [European Journal of Organic Chemistry, 2021, vol. 2021, # 14, p. 2103 - 2106]
[12]Oestreich, Martin; Richter, Sven C. [European Journal of Organic Chemistry, 2021, vol. 2021, # 14, p. 2103 - 2106]
  • 42
  • [ 939-27-5 ]
  • [ 1391853-96-5 ]
  • [ 1391854-16-2 ]
YieldReaction ConditionsOperation in experiment
73% Stage #1: 2-ethylnaphthalene; (R)-2,2,2-trichloro-1-phenylethyl ((methylsulfonyl)oxy)carbamate In ethyl acetate at 23℃; for 0.0833333h; Stage #2: With potassium acetate In ethyl acetate at 23℃; for 2h; optical yield given as %de; stereoselective reaction;
  • 43
  • [ 1592-38-7 ]
  • [ 75-16-1 ]
  • [ 939-27-5 ]
  • [ 91-57-6 ]
YieldReaction ConditionsOperation in experiment
1: 72% 2: 8% With bis(1,5-cyclooctadiene)nickel (0); 2-[2-(dicyclohexylphosphino)-phenyl]-1-methyl-1H-indole In toluene at 80℃; for 12h; Schlenk technique; Sealed tube;
1: 68% 2: 9% With bis(acetylacetonate)nickel(II); 1,1'-bis(dicyclohexylphosphinocyclopentadienyl)iron In toluene at 60℃; for 24h; Inert atmosphere;
  • 44
  • [ 939-27-5 ]
  • [ 1315310-81-6 ]
  • [ 1407156-69-7 ]
YieldReaction ConditionsOperation in experiment
75% With copper(ll) sulfate pentahydrate; sodium L-ascorbate In N,N-dimethyl-formamide at 90℃; for 48h; Inert atmosphere;
  • 45
  • [ 939-27-5 ]
  • [ 30159-69-4 ]
  • [ 13112-58-8 ]
  • 46
  • [ 939-27-5 ]
  • [ 1378332-77-4 ]
YieldReaction ConditionsOperation in experiment
53% With (S,S)-chloro[2,2'-[1,2-cyclohexanediylbis(nitrilomethylidyne)]bis-[4,6-bis(1,1-dimethylethyl)phenolato]](2-)-N,N',O,O'-manganese; iodosylbenzene; triethylamine tris(hydrogen fluoride) In acetonitrile at 50℃; Schlenk technique; Inert atmosphere;
With (S,S)-chloro[2,2'-[1,2-cyclohexanediylbis(nitrilomethylidyne)]bis-[4,6-bis(1,1-dimethylethyl)phenolato]](2-)-N,N',O,O'-manganese; iodosylbenzene; triethylamine tris(hydrogen fluoride) In acetonitrile at 50℃; Schlenk technique; Inert atmosphere;
  • 47
  • 1-(naphthalen-2-yl)ethanone N-tosylhydrazone [ No CAS ]
  • [ 939-27-5 ]
YieldReaction ConditionsOperation in experiment
85 %Chromat. With methanol; palladium 10% on activated carbon; hydrogen; potassium carbonate at 65℃; for 24h; 1 4.2. General procedure for the N-tosylhydrazine mediated reductive deoxygenation of aldehydes and ketones with Pd/C-H2 General procedure: The aldehyde or ketone (0.5mmol), N-tosylhydrazine (98mg, 1.05equiv), and MeOH (10mL) were placed in a 50mL two-necked round bottle equipped with magnetic stirring bar and condenser. The reaction was heated at 60°C until aldehyde or ketone was completely consumed. (For diarylmethanones, the preparation of corresponding N-tosylhydrazones often need 1mol% TsOH·H2O as catalyst.) After cooling to the room temperature, 10% w/w of Pd/C (26.5mg, 5mol%) and K2CO3 (276mg, 4equiv) were added. The mixture was degassed by ‘pump-freeze-thaw’ cycles (×3) and flushed with hydrogen. The resulting solution was heated at 65°C for 24h under 1atm of hydrogen atmosphere. Resulting product mixture was filtered through a short path of silica gel, eluting with ethyl acetate. The volatile compounds were removed in vacuo and the crude residue was purified by column chromatography (SiO2, hexane) or analyzed by GC.
  • 48
  • [ 939-27-5 ]
  • [ 27544-18-9 ]
YieldReaction ConditionsOperation in experiment
100 % ee With hydrogenchloride; ferrocenium(III) tetrafluoroborate; ethylbenzene dehydrogenase In water; <i>tert</i>-butyl alcohol at 30℃; Enzymatic reaction; enantioselective reaction; 2. Experimental section General procedure: 2.1. Sample preparation Ethylbenzene dehydrogenase was purified from ethylbenzene-grown A. aromaticum cells as previously described [11,23]. The enzyme assays were routinely conducted at an optimum pH of 7.5 at 30 °C in 20 ml of 100 mM Tris/HCl containing 200 μM ferrocenium (III) tetrafluoroborate and ethylbenzene dehydrogenase (100-300 μl of app. 1 mg/ml protein solution). The reactions were initiated by adding 100 μl of a stock solution of the respective substrate in tert-butanol (a list of substrates, their purities and producers is available in the Supporting Information). After an overnight incubation, the reaction mixtures were extracted from the water phase by solid-phase extraction using either C18 Polar Plus (J.T. Baker from Avantor Performance Materials, US) or polystyrene/divinylbenzene (PS/DVB) copolymers solid phase extraction (SPE) columns (Strata-X from Phenomenex, US or the equivalent Chromabond HR-X from Macherey-Nagel, Germany), which were eluted with 0.5 ml of isopropanol. The only exception to the procedure was the 2-ethyl-1H-pyrrole reaction mixtures (22). Due to the high polarity of the product derived from this compound, we were unable to concentrate the sample and exchange the solvent by SPE. Therefore, the enzyme was precipitated by the addition of 50% methanol, and it was removed by centrifugation. The supernatant was directly analyzed by non-chiral reversed-phase (RP)-LC.
  • 49
  • [ 28172-58-9 ]
  • [ 939-27-5 ]
  • 2-(4-methoxyphenyl)-4-(2-(naphthalen-2-yl)ethyl)-4-phenyloxazol-5(4H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With palladium diacetate In 1,4-dioxane at 90℃; for 24h; Inert atmosphere; Glovebox; Sealed tube; chemoselective reaction;
  • 50
  • [ 67-71-0 ]
  • [ 1592-38-7 ]
  • [ 939-27-5 ]
YieldReaction ConditionsOperation in experiment
77% With platinum on carbon; potassium <i>tert</i>-butylate; hydrogen In toluene for 24h; Inert atmosphere; Reflux;
71% With C24H20ClN2OPRu; potassium <i>tert</i>-butylate; hydrogen In tetrahydrofuran at 125℃; for 20h;
  • 51
  • [ 85102-56-3 ]
  • [ 939-27-5 ]
YieldReaction ConditionsOperation in experiment
98% With triethylsilane; tris(pentafluorophenyl)borate In chloroform-d1 at 20℃; chemoselective reaction;
  • 52
  • 2-methyl-2-(naphthalen-2-yl)-1,3-dithiane [ No CAS ]
  • [ 939-27-5 ]
YieldReaction ConditionsOperation in experiment
93% With triethylsilane; tris(pentafluorophenyl)borate In chloroform-d1 at 20℃; chemoselective reaction;
88% Stage #1: 2-methyl-2-(naphthalen-2-yl)-1,3-dithiane With chloro-trimethyl-silane; sodium iodide In dichloromethane at 35℃; for 40h; Inert atmosphere; Green chemistry; Stage #2: With water In dichloromethane at 20℃; Inert atmosphere; Green chemistry;
  • 53
  • 4-chlorophenyl(1-(naphthalene-6-yl)ethyl)sulfane [ No CAS ]
  • [ 939-27-5 ]
YieldReaction ConditionsOperation in experiment
85% With triethylsilane; tris(pentafluorophenyl)borate In chloroform-d1 at 20℃; for 1h; chemoselective reaction;
  • 54
  • C22H32S [ No CAS ]
  • [ 939-27-5 ]
YieldReaction ConditionsOperation in experiment
95% With triethylsilane; tris(pentafluorophenyl)borate In chloroform-d1 at 20℃; for 1h; chemoselective reaction;
  • 55
  • methyl (E)-2-(1-(naphthalen-2-yl)ethylidene)hydrazine-1-carboxylate [ No CAS ]
  • [ 939-27-5 ]
YieldReaction ConditionsOperation in experiment
86% With potassium hydroxide In 2,2'-[1,2-ethanediylbis(oxy)]bisethanol at 140℃; for 4h; 2-Ethylnaphthalene KOH (0.46 g, 8.3 mmol) was added to triethylene glycol (5.0 mL) and heated to 100 °C until itdissolved to give a red/orange solution. Methyl (E)-2-(1-(naphthalen-2-yl)ethylidene)hydrazine-1-carboxylate (0.50 g, 2.1 mmol) was added in one portion and the reaction heated at 140 °C for 4hours. The reaction was allowed to cool, diluted with water and the aqueous phase extracted intoEt2O (2 × 10 mL). The organic phase was dried (MgSO4), filtered and the solvent removed in vacuo.The crude product was purified by flash column chromatography (5% Et2O/pentane) to give 2-ethylnapthalene as a pale yellow oil (0.28 g, 1.8 mmol, 86%)1H NMR (400 MHz, CDCl3) 7.77-7.71 (3H, m, CHAr), 7.58 (1H, s, CHAr), 7.42-7.34 (2H, m, CHAr), 7.29(1H, dd, J = 8.4, 1.6 Hz, CHAr), 2.76 (2H, q, J = 7.6 Hz, CH2CH3), 1.27 (3H, t, J = 7.6 Hz, CH2CH3).13C NMR (100 MHz, CDCl3) 140.7 (CAr), 132.6 (CAr), 130.9 (CAr), 126.7 (CArH), 126.5 (CArH), 126.4(CArH), 126.0 (CArH), 124.7 (CArH), 124.5 (CArH), 123.9 (CArH), 28.0 (CH2CH3), 14.5 (CH2CH3).νmax (neat) cm-1 2924, 1491, 1090..
  • 56
  • [ 939-27-5 ]
  • [ 2243-82-5 ]
  • 57
  • [ 93-04-9 ]
  • [ 97-93-8 ]
  • [ 939-27-5 ]
YieldReaction ConditionsOperation in experiment
97% Stage #1: 2-Methoxynaphthalene With bis(1,5-cyclooctadiene)nickel (0); 1,2-bis-(dicyclohexylphosphino)ethane In di-isopropyl ether; toluene at 20℃; for 0.0833333h; Glovebox; Inert atmosphere; Stage #2: triethylaluminum In di-isopropyl ether; toluene at 100℃; for 12h; Glovebox; Inert atmosphere;
  • 58
  • [ 10467-10-4 ]
  • [ 93-04-9 ]
  • [ 939-27-5 ]
YieldReaction ConditionsOperation in experiment
93% With bis(1,5-cyclooctadiene)nickel(0); 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 100℃; for 14h; Inert atmosphere; Glovebox; Sealed tube;
  • 59
  • [ 7677-24-9 ]
  • [ 939-27-5 ]
  • [ 146744-11-8 ]
YieldReaction ConditionsOperation in experiment
65% With (3aR,3a'R,8aS,8a'S)-2,2'-(cyclopentane-1,1-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole); copper (I) acetate; N-fluorobis(benzenesulfon)imide In benzene at 20℃; Inert atmosphere; enantioselective reaction;
  • 60
  • [ 97-94-9 ]
  • [ 93-04-9 ]
  • [ 939-27-5 ]
YieldReaction ConditionsOperation in experiment
88% With bis(1,5-cyclooctadiene)nickel (0); cesium fluoride; tricyclohexylphosphine In di-isopropyl ether at 110℃; for 60h; Sealed tube; Inert atmosphere;
  • 61
  • [ 66-99-9 ]
  • [ 31729-70-1 ]
  • [ 939-27-5 ]
YieldReaction ConditionsOperation in experiment
75% With Wilkinson's catalyst; hydrogen In tetrahydrofuran at 25℃;
  • 62
  • [ 1469537-96-9 ]
  • [ 97-93-8 ]
  • [ 939-27-5 ]
YieldReaction ConditionsOperation in experiment
94% With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In 1,4-dioxane at 110℃; for 24h; Schlenk technique; Inert atmosphere; 4.2 Typical procedure for the reaction of aryl(or 2-menaphthyl)trimethylammonium triflates with organoaluminum reagents General procedure: A Schlenk tube was successively charged with aryl(or 2-menaphthyl)trimethylammonium triflate (0.5 mmol), Ni(dppp)Cl2 (5 mol%), dioxane (3 mL), and organoaluminum reagent (0.75 mmol). The mixture was heated at 110 °C (bath temperature) for 24 h with stirring and then cooled to room temperature. Water (10 mL) was added and the resultant mixture was extracted with Et2O (10 mL×3). The combined organic phases were dried over anhydrous Na2SO4, concentrated by rotary evaporation, and purified by column chromatography on silica gel.
  • 63
  • [ 1416982-18-7 ]
  • [ 75-24-1 ]
  • [ 939-27-5 ]
YieldReaction ConditionsOperation in experiment
88% With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In 1,4-dioxane at 110℃; for 24h; Schlenk technique; Inert atmosphere; 4.2 Typical procedure for the reaction of aryl(or 2-menaphthyl)trimethylammonium triflates with organoaluminum reagents General procedure: A Schlenk tube was successively charged with aryl(or 2-menaphthyl)trimethylammonium triflate (0.5 mmol), Ni(dppp)Cl2 (5 mol%), dioxane (3 mL), and organoaluminum reagent (0.75 mmol). The mixture was heated at 110 °C (bath temperature) for 24 h with stirring and then cooled to room temperature. Water (10 mL) was added and the resultant mixture was extracted with Et2O (10 mL×3). The combined organic phases were dried over anhydrous Na2SO4, concentrated by rotary evaporation, and purified by column chromatography on silica gel.
  • 64
  • [ 1503-86-2 ]
  • [ 6107-37-5 ]
  • [ 939-27-5 ]
YieldReaction ConditionsOperation in experiment
99% With bis(1,5-cyclooctadiene)nickel (0); 1,2-bis-(dicyclohexylphosphino)ethane In tetrahydrofuran; di-isopropyl ether at 70℃; for 18h;
  • 65
  • [ 941-55-9 ]
  • [ 939-27-5 ]
  • (R)-4-methyl-N-(1-(naphthalen-2-yl)ethyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With D-glucose; catalase; glucose oxidase In dimethyl sulfoxide at 20℃; Sealed tube; Inert atmosphere; Enzymatic reaction; enantioselective reaction; Intermolecular C-H amination in whole E. coli cells. General procedure: For amination bioconversions, the cells containing the P411 variant, at OD600 of 30 in M9-N media(grown as described above), were degassed by sparging with argon in sealed 6-mlcrimp vials for at least 40 min. Separately, a glucose solution (250 mM in M9-N) was degassed by sparging with argon for at least 10 min. An oxygen depletion system(20 μl of a stock solution containing 14,000 Uml-1 catalase and 1,000 Uml-1glucose oxidase in 0.1 M KPi, pH 8.0) was added to 2-ml crimp vials. All solutions were uncapped and transferred into an anaerobic chamber. Resuspended cells (320μl) were added to the vials, followed by glucose (40 μl, 250 mM in M9-N), alkane(10 μl of a DMSO stock), and tosyl azide (10 μl of a DMSO stock). Final concentrations were typically 2.5-5.0 mM alkane, 5.0 mM tosyl azide, and 25 mMglucose; final reaction volume was 400 μl. The vials were sealed, removed from the anaerobic chamber, and shaken at room temperature and 40 rpm for 16-20 h. The reactions were quenched by addition of acetonitrile (400 μl) and internal standard (10 μl of a DMSO stock). This mixture was then transferred to a microcentrifuge tube and centrifuged at 20,000g for 10 min. The supernatant was transferred to a vialand analysed by HPLC for yield. Reaction samples were extracted with cyclohexaneand analysed by chiral SFC (supercritical fluid chromatography) for enantiomeric excess (e.e.). Yield is calculated as mM reaction product divided by mM starting material; TON is calculated as mM reaction product divided by mM P411,as determined by the CO-binding assay following cell lysis. e.e. is calculated as(major enantiomer-minor enantiomer)/(major enantiomer + minor enantiomer).
  • 66
  • [ 939-27-5 ]
  • [ 7228-47-9 ]
YieldReaction ConditionsOperation in experiment
95% With C20H24B10Br2Cl2FeN6; dihydrogen peroxide In methanol at 20℃; for 8h; 16 Dissolve 2-ethylnaphthalene (1.0mmol), iron complex 5 (0.02mmol) and H2O2 (1.3mmol) in 2mL of methanol and react at room temperature for 8 hours.After the reaction, the concentrated reaction solution was directly separated by silica gel column chromatography and dried to the same quality.The corresponding product C12H12O was obtained (95% yield).
With cytochrome P450 monooxygenase enzyme CYP101B1 Enzymatic reaction; enantioselective reaction;
With phosphoric acid; dihydrogen peroxide; Aliquat 336; ortho-tungstic acid at 75℃; for 6h;
  • 67
  • [ 97-94-9 ]
  • [ 82408-29-5 ]
  • [ 939-27-5 ]
YieldReaction ConditionsOperation in experiment
72% With bis(1,5-cyclooctadiene)nickel (0); cesium fluoride; 1,2-bis-(dicyclohexylphosphino)ethane In hexane; toluene at 150℃; for 48h; Sealed tube; Glovebox; chemoselective reaction;
  • 68
  • [ 1619256-41-5 ]
  • [ 939-27-5 ]
  • 3-ethylidene-1,2,3,4-tetrahydronaphthalen-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 86% 2: 7% With tin (IV) chloride pentahydrate In ethyl acetate at 20℃; for 36h; General procedures to perform the ene reactions: With SnCl4·5H2O General procedure: A stirred solution of an O-propenyl arene aldehyde (1equiv) in dry solvent (10mL/mmol) was stirred with SnCl4·5H2O (50mol%) in stoppered reaction flask. After completion of the reaction, as monitored by TLC, it was quenched with saturated solution of sodium bicarbonate (5mL/mmol). Usual work-up of the reaction mixture with EA or DCM furnished the mixture of products. Products were purified by column chromatography on basic alumina.
  • 69
  • [ 133339-20-5 ]
  • [ 939-27-5 ]
YieldReaction ConditionsOperation in experiment
97 %Chromat. With bis(1,5-cyclooctadiene)nickel (0); 1,3-bis(2,4,6-trimethylphenyl)4,5-dimethyl-1,3-dihydro-2H-imidazol-2-ylidene; diisopropopylaminoborane; sodium acetate In toluene at 180℃; for 18h;
40 %Chromat. With [Ni(0)(PCy3)2]2N2 In tetrahydrofuran at 50℃; for 7h; Schlenk technique; Inert atmosphere; Sealed tube;
  • 70
  • [ 89113-45-1 ]
  • [ 939-27-5 ]
YieldReaction ConditionsOperation in experiment
94 %Chromat. With bis(1,5-cyclooctadiene)nickel (0); 1,3-bis(2,4,6-trimethylphenyl)4,5-dimethyl-1,3-dihydro-2H-imidazol-2-ylidene; diisopropopylaminoborane; sodium acetate In toluene at 180℃; for 18h;
  • 71
  • [ 7433-79-6 ]
  • [ 925-90-6 ]
  • [ 939-27-5 ]
YieldReaction ConditionsOperation in experiment
93% With bis(1,5-cyclooctadiene)nickel (0); 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 90℃; for 10h; Inert atmosphere; Schlenk technique; Sealed tube;
  • 72
  • [ 3238-55-9 ]
  • [ 580-13-2 ]
  • [ 939-27-5 ]
YieldReaction ConditionsOperation in experiment
80% With 2.9-dimethyl-1,10-phenanthroline; palladium(II) trifluoroacetate; potassium <i>tert</i>-butylate In toluene at 120℃; for 20h; Inert atmosphere;
  • 73
  • [ 939-27-5 ]
  • [ 3066-71-5 ]
  • cyclohexyl (E)-3-(7-ethylnaphthalen-2-yl)acrylate [ No CAS ]
  • cyclohexyl (E)-3-(6-ethylnaphthalen-2-yl)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper(II) 2-ethylhexanoate; chlorobis(ethylene)rhodium(I) dimer; silver sulfate In cyclohexane at 140℃; for 24h; Inert atmosphere; Overall yield = 72 %; 2-1. General procedure for Rh-catalyzed non-directed alkenylation (Scheme 1 and 2) General procedure: A screw-top glass tube was charged with aromatic compound 1 (1.25 mmol, 5.0 eq.), alkene 2 (0.25 mmol, 1.0 eq.), [RhCl(C2H2)2]2 (2.5 mol %), Cu(eh)2 (0.5 mmol, 2.0 eq.), and Ag2SO4 (0.5mmol, 2.0 eq.). Cyclohexane (3.0 mL) was added via syringe, and the resulting mixture was stirred at 140 °C for 24 h. After cooling to room temperature, the reaction mixture was extracted with EtOAc several times. The combined organic layers was washed with H2O containing ethylenediamine (ca. 1.0 mL), dried over Na2SO4, and concentrated in vacuo. The residue was subjected to silica gel column chromatography to give the corresponding product 3.
  • 74
  • [ 939-27-5 ]
  • [ 52193-85-8 ]
YieldReaction ConditionsOperation in experiment
55% Stage #1: 2-ethylnaphthalene With ketoreductase-P3-B03; oxygen; NADPH; 9-(2-mesityl)-10-methylacridinium perchlorate In water; acetonitrile at 23℃; for 24h; Irradiation; Enzymatic reaction; Stage #2: With isopropyl alcohol In water; acetonitrile Enzymatic reaction; enantioselective reaction;
  • 75
  • [ 939-27-5 ]
  • (E)-2-(2-nitrovinyl)naphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% Stage #1: 2-ethylnaphthalene With potassium phosphate; barium(II) nitrate; trifluorormethanesulfonic acid; bathophenanthroline; copper (I) acetate In N,N-dimethyl-formamide for 0.0833333h; Inert atmosphere; Stage #2: With ammonium peroxydisulfate; silver trifluoroacetate In N,N-dimethyl-formamide at 95℃; for 24h; Inert atmosphere; Sealed tube; 3 Example 3 First, put a pressure tube with a magnet in an ice water bath, vacuum and fill with nitrogen three times,Add 0.5mL dry DMF and 6mmol CF3SO3H in a nitrogen atmosphere and seal,After stirring for 5 minutes, let it stand at room temperature and stir for 5 minutes. then,Add 0.6mmol Ba(NO3)2, 0.015mmol CuOAc in a nitrogen atmosphere,0.015mmol 4,7-diphenyl-1,10-phenanthroline,0.3mmol K3PO4 and 0.5mL dry DMF in a pressure tube, stir for 5 minutes,Then add 0.45mmol(NH4)2S2O8 and 0.06mmol CF3COOAg, after stirring, add 0.3mmol 2-ethylnaphthalene and 1.0mL dry DMF mixed solution and stir for 5 minutes,In the above steps, one of the substances in the pressure tube is in a stirring state.The reaction mixture was evacuated and filled with inert gas three times and the pressure tube was sealed,Place in an oil bath at 95°C. After reacting for 24 hours, cool to room temperature,Add an appropriate amount of saturated sodium bicarbonate solution to make the reaction liquid neutral, extract three times with ethyl acetate, combine the organic phases, dry with anhydrous magnesium sulfate, filter and concentrate.The concentrate was separated and purified by column chromatography, and the yield of the pure product was 52%.
  • 76
  • [ 939-27-5 ]
  • [ 873-31-4 ]
  • 2-(4-(2-chlorophenyl)but-3-yn-2-yl)naphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% Stage #1: 2-ethylnaphthalene; 2-chlorophenylacetylene With [Cl2NN]Cu(benzene) In chlorobenzene for 0.0833333h; Inert atmosphere; Glovebox; Stage #2: With di-tert-butyl peroxide In chlorobenzene at 90℃; Inert atmosphere; Glovebox; Sealed tube;
  • 77
  • [ 2949-26-0 ]
  • [ 939-27-5 ]
YieldReaction ConditionsOperation in experiment
77% With (R)-(-)-5,5'-bis[di(3,5-ditert-butyl-4-methoxyphenyl)phosphino]-4,4'-bi-1,3-benzodioxole; methyl dimethoxy silane; copper (II) acetate In tetrahydrofuran; isopropanol at 60℃; for 14h; Glovebox; 1; 2 General procedure for transfer hydrogenation (C). General procedure: In a N2 filled glovebox, (R or S)-DTBM-SEGPHOS (10.4 mg, 0.0088 mmol, 0.022 eq.), Cu(OAc)2 (40 μL of a 0.2 M solution in THF, 0.008 mmol, 0.02 eq.), and THF (0.16 mL) were added to an oven-dried 2- dram vial followed by dropwise addition of dimethoxy(methyl)silane (247 μL, 2 mmol, 5 eq.). A color change from green/blue to orange was observed while stirring for 15 minutes. In a separate oven-dried 1-dram vial was added the alkyne substrate (0.4 mmol, 1 eq.), THF (0.2 mL), and either ethanol or 2-propanol (2.4-5 eq. based on substrate). The solution in the 1- dram vial was added dropwise over 20 seconds to the 2-dram vial. The total volume of THF was calculated based on having a final reaction concentration of 1M based on the alkyne substrate. The 2-dram vial was capped with a red pressure relief cap, taken out of the glovebox, and stirred for 9-24 h at the appropriate temperature at which point the reaction was filtered through a 1” silica plug with 20 mL of Et2O followed by 80 mL of Et2O to elute the remaining product into a 200 mL round bottom flask. After removing the Et2O by rotary evaporation, the crude product was isolated by flash column chromatography.
73% With (S)-(+)-5,5’-bis[di(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-4,4’-bi-1,3-benzodioxole; methyl dimethoxy silane; copper (II) acetate; isopropanol In tetrahydrofuran at 60℃; for 14h; Sealed tube; Inert atmosphere;
  • 78
  • [ 56059-50-8 ]
  • [ 2386-64-3 ]
  • [ 939-27-5 ]
  • naphthalen-2-yl 4-ethylbenzenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With 1,3-dimethyl-2-imidazolidinone; iron(III)-acetylacetonate In tetrahydrofuran at 0℃; for 0.166667h; Schlenk technique; Inert atmosphere; Green chemistry; 4.2. General Procedure for Iron-Catalyzed C(sp2)-C(sp3) Cross-Coupling General procedure: An oven-dried vial equipped with a stir bar was charged with a sulfonate ester substrate(neat, typically, 0.50 mmol, 1.0 equiv) and Fe(acac)3 (typically, 5 mol%), placed undera positive pressure of argon, and subjected to three evacuation/backfilling cycles undervacuum. Tetrahydrofuran (0.15 M) and ligand were sequentially added with vigorousstirring at room temperature, the reaction mixture was cooled to 0 C, a solution of Grignardreagent (typically, 1.2 equiv) was added dropwise with vigorous stirring, and thereaction mixture was stirred for the indicated time at 0 C. After the indicated time, thereaction mixture was diluted with HCl (1.0 N, 1.0 mL) and Et2O (1 30 mL); the organiclayer was extracted with HCl (1.0 N, 2 10 mL), dried, and concentrated. The samplewas analyzed by 1H NMR (CDCl3, 400 MHz) and GC-MS to obtain conversion, yield, andselectivity using internal standard and comparison with authentic samples. Purification bychromatography on silica gel (EtOAc/hexanes = 1/4) afforded the title product.
  • 79
  • [ 19219-99-9 ]
  • [ 939-27-5 ]
  • C20H17NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% Stage #1: 2-ethylnaphthalene With n-butyllithium; potassium <i>tert</i>-butylate In tetrahydrofuran; hexane at -40℃; for 0.166667h; Stage #2: With zinc(II) chloride In tetrahydrofuran; hexane at 20℃; Stage #3: 2-methyl-5-chlorobenzoxazole With tris-(dibenzylideneacetone)dipalladium(0); XPhos In tetrahydrofuran at 60℃;
  • 80
  • [ 939-27-5 ]
  • [ 3032-92-6 ]
  • 4-(3-(naphthalen-2-yl)but-1-yn-1-yl)benzonitrile [ No CAS ]
  • (R)-4-(3-(naphthalen-2-yl)but-1-yn-1-yl)benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% ee With copper(I) thiophene-2-carboxylate; N-(tert-butyl)-N-fluoro-4-(trifluoromethyl)benzenesulfonamide; N-(2-((3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazol-2-yl)-3-(trifluoromethyl)phenyl)-2-(diphenylphosphanyl)benzamide; caesium carbonate In chlorobenzene at 0℃; Schlenk technique; Inert atmosphere; Overall yield = 62 percent; Overall yield = 16.0 mg; enantioselective reaction;
  • 81
  • [ 939-27-5 ]
  • [ 3032-92-6 ]
  • (R)-2-(4-phenylbut-3-yn-2-yl)naphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% ee With copper(I) thiophene-2-carboxylate; N-(tert-butyl)-N-fluoro-4-(trifluoromethyl)benzenesulfonamide; N-(2-((3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazol-2-yl)-3-(trifluoromethyl)phenyl)-2-(diphenylphosphanyl)benzamide; caesium carbonate In chlorobenzene at 0℃; Schlenk technique; Inert atmosphere; enantioselective reaction;
  • 82
  • [ 939-27-5 ]
  • [ 58464-06-5 ]
YieldReaction ConditionsOperation in experiment
97% With diisopropyl phosphite; potassium chloride; N-fluorobis(benzenesulfon)imide; copper(l) chloride; {3aS-[2(3'aR*,8'aS*),3aα,8aα]-2,2'-(cyclopropylidene)-bis{3a,8a-dihydro-8H-indeno[1,2-d]-oxazole} In chlorobenzene at 20℃; for 16h; Sealed tube; Glovebox; Inert atmosphere;
  • 83
  • [ 1605319-66-1 ]
  • [ 939-27-5 ]
YieldReaction ConditionsOperation in experiment
41% With [Ni(0)(PCy3)2]2N2; magnesium bromide ethyl etherate In tetrahydrofuran; toluene at 0℃; for 7h; Inert atmosphere; Schlenk technique; Sealed tube;
  • 84
  • [ 939-27-5 ]
  • C8H5BrF2 [ No CAS ]
  • C20H16F2 [ No CAS ]
  • C20H16F2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With nickel(II) bromide dimethoxyethane; (3aR,3a’R,8aS,8a’S)-2,2’-(cyclopropane-1,1-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]-oxazole); [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; potassium carbonate In ethyl acetate at 15℃; for 24h; Irradiation;
  • 85
  • [ 939-27-5 ]
  • [ 65-85-0 ]
  • [ 6860-93-1 ]
YieldReaction ConditionsOperation in experiment
64% With 2.9-dimethyl-1,10-phenanthroline; [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; copper (II) acetate; N-fluorobis(benzenesulfon)imide In acetonitrile at 35℃; for 16h; Inert atmosphere; Sealed tube; Irradiation; chemoselective reaction;
Same Skeleton Products
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