[ CAS No. 345-92-6 ] {[proInfo.proName]}

Name: 345-92-6|Bis(4-Fluorophenyl)methanone|98%
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Product Details of [ 345-92-6 ]

CAS No. :	345-92-6	MDL No. :	MFCD00000353
Formula :	C₁₃H₈F₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LSQARZALBDFYQZ-UHFFFAOYSA-N
M.W :	218.20	Pubchem ID :	9582
Synonyms :

Calculated chemistry of [ 345-92-6 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	56.23
TPSA :	17.07 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.92 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.34
Log Po/w (XLOGP3) :	3.82
Log Po/w (WLOGP) :	4.04
Log Po/w (MLOGP) :	3.8
Log Po/w (SILICOS-IT) :	4.21
Consensus Log Po/w :	3.64

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.02
Solubility :	0.0207 mg/ml ; 0.000095 mol/l
Class :	Moderately soluble
Log S (Ali) :	-3.87
Solubility :	0.0292 mg/ml ; 0.000134 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.43
Solubility :	0.000813 mg/ml ; 0.00000372 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.44

Safety of [ 345-92-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 345-92-6 ]

* 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.

Upstream synthesis route of [ 345-92-6 ]
Downstream synthetic route of [ 345-92-6 ]

[ 345-92-6 ] Synthesis Path-Upstream 1~12

1
[ 345-92-6 ]
[ 27469-60-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1822 - 1826
[2] Journal of Enzyme Inhibition and Medicinal Chemistry, 2014, vol. 29, # 2, p. 205 - 214
[3] Synthetic Communications, 2014, vol. 44, # 5, p. 600 - 609
[4] Medicinal Chemistry Research, 2014, vol. 23, # 6, p. 3207 - 3219
[5] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 10, p. 2526 - 2530

2
[ 110-85-0 ]
[ 345-92-6 ]
[ 27469-60-9 ]

Reference： [1] Journal of Molecular Structure, 2018, vol. 1154, p. 72 - 78

3
[ 345-92-6 ]
[ 26864-56-2 ]

Reference： [1] Tetrahedron, 2001, vol. 57, # 8, p. 1631 - 1637
[2] Tetrahedron, 2001, vol. 57, # 8, p. 1631 - 1637

4
[ 345-92-6 ]
[ 58113-36-3 ]

Reference： [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 13, p. 2047 - 2052

5
[ 345-92-6 ]
[ 345-90-4 ]

Reference： [1] Patent: US6248766, 2001, B1,
[2] Letters in Drug Design and Discovery, 2010, vol. 7, # 9, p. 661 - 664

6
[ 345-92-6 ]
[ 365-24-2 ]

Yield	Reaction Conditions	Operation in experiment
96%	With sodium tetrahydroborate In methanol at 20℃;	General procedure: NaBH4 (0.6mol) was added to a stirred solution of benzophenones (1.0 mol)in methanol (2 vol) portionwise at room temperature for 45 min. The mixture was stirred for 2–3 h at ambient temperature (completion of reaction was monitoredby TLC), and was diluted with water (750 ml), acidified with acetic acid to pH 4,and extracted with dichloromethane (2x400 ml). The organic layer was washed with water (200 ml) and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to get pure benzhydrol derivatives as a white to off-white solid in 93–97percent yield. To the benzhydrol derivatives (1.0 mol) in toluene (370 ml) was added concentrated HCl (35percent in H2O, 370 ml) and tetrabutylammonium bromide(0.01 mol) at room temperature under stirring. Stirring was continued at 40–45 °C for 6–7 h. After completion of the reaction as indicated by TLC, the mixture was cooled to room temperature. The organic layer was separated and concentrated under vacuum to obtain crude benzhydryl chloride derivatives as a light brown liquid in 95–97percent yield. To this benzhydryl chloride (0.96 mol) derivatives in toluene (380 ml) was added anhydrous piperazine (5.0 mol) at 60–70 °C for 45–60 min. The resulting mixture was heated under stirring at 90–100 °C for 8–10 h. The mixture was cooled after completion of the reaction. Water (380 ml) was added, and the organic layer was separated. The latter was washed with a 1:1 mixture of concentrated HCl/water(2x350 ml) and neutralized with 20percent NaOH solution (750 ml). The water layer was re-extracted into toluene (2x300 ml), dried over anhydrous sodium sulfate, and concentrated under vacuum to result pure diphenylmethylpiperazine compounds (2a–c) as a white to off-white solid with yields up to 88percent.
89%	With lithium tert-butoxide In dimethyl amine at 60℃; for 5 h;	A. In a reaction vessel equipped with a reflux condenser, 0.23 mol of 4,4-difluorobenzophenone, 0.31 mol of lithium isobutoxide, 65percent of dimethylamine solution and 260 ml of dimethylamine solution were added, and the temperature of the solution was increased to 60 , refluxing reaction 5h;B, save the distillate temperature at 45 , vacuum distillation, steamed out of dimethylamine, the remaining solution by adding 300ml mass fraction of 35percent ethyl acetate solution, precipitation of oil;C, pour out the oil and then add 350ml mass fraction of 60percent cyclohexane solution, shake, precipitate solid, filter, 75percent acetonitrile solution in the recrystallization, mass fraction of 50percent dichloromethane solution washing , The mass fraction of 25percent triethylamine solution washing, anhydrous magnesium sulfate dehydrating agent dehydration, in colorless crystal two pairs of fluorophenyl methanol 45.03g, yield 89percent.

Reference： [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 28, p. 5094 - 5096
[2] Synthesis, 2010, # 12, p. 1989 - 1991
[3] Synthetic Communications, 2014, vol. 44, # 5, p. 600 - 609
[4] Organic Letters, 2000, vol. 2, # 5, p. 659 - 661
[5] Patent: , 2016, , . Location in patent: Paragraph 0016; 0018; 0019; 0020; 0021; 0022
[6] Chemistry - An Asian Journal, 2010, vol. 5, # 7, p. 1687 - 1691
[7] Advanced Synthesis and Catalysis, 2015, vol. 357, # 14-15, p. 3115 - 3120
[8] Pharmazie, Beih. 2 <1949> 147,
[9] Canadian Journal of Research, Section B: Chemical Sciences, 1950, vol. 28, p. 56,58
[10] Journal of the American Chemical Society, 1950, vol. 72, p. 4282
[11] Journal of the American Chemical Society, 1957, vol. 79, p. 5804,5807
[12] Chemical and pharmaceutical bulletin, 2003, vol. 51, # 2, p. 122 - 133
[13] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 14, p. 3691 - 3695
[14] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 22, p. 4915 - 4918
[15] Letters in Drug Design and Discovery, 2010, vol. 7, # 2, p. 109 - 115
[16] Letters in Drug Design and Discovery, 2010, vol. 7, # 9, p. 661 - 664
[17] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1822 - 1826
[18] Chinese Journal of Chemistry, 2011, vol. 29, # 6, p. 1180 - 1184
[19] Chemical Communications, 2012, vol. 48, # 38, p. 4567 - 4569
[20] Chemistry - A European Journal, 2012, vol. 18, # 18, p. 5701 - 5714
[21] Journal of Enzyme Inhibition and Medicinal Chemistry, 2014, vol. 29, # 2, p. 205 - 214
[22] Medicinal Chemistry Research, 2014, vol. 23, # 6, p. 3207 - 3219
[23] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 10, p. 2526 - 2530
[24] Organic Electronics: physics, materials, applications, 2017, vol. 41, p. 122 - 129
[25] Journal of the American Chemical Society, 2018, vol. 140, # 6, p. 2292 - 2300

7
[ 345-92-6 ]
[ 365-24-2 ]

Reference： [1] Organic Letters, 2016, vol. 18, # 6, p. 1306 - 1309

8
[ 462-06-6 ]
[ 403-43-0 ]
[ 345-71-1 ]
[ 342-25-6 ]
[ 345-92-6 ]

Reference： [1] Chemical Communications, 2004, # 12, p. 1368 - 1369

9
[ 56-23-5 ]
[ 462-06-6 ]
[ 342-25-6 ]
[ 345-92-6 ]

Reference： [1] Russian Chemical Bulletin, 2001, vol. 50, # 7, p. 1208 - 1213

10
[ 345-92-6 ]
[ 289656-45-7 ]

Reference： [1] Organic Process Research and Development, 2012, vol. 16, # 8, p. 1385 - 1392

11
[ 345-92-6 ]
[ 289656-45-7 ]
[ 386-95-8 ]

Reference： [1] Organic Process Research and Development, 2012, vol. 16, # 8, p. 1385 - 1392

12
[ 345-92-6 ]
[ 289656-45-7 ]
[ 386-95-8 ]
[ 1391151-86-2 ]

Reference： [1] Organic Process Research and Development, 2012, vol. 16, # 8, p. 1385 - 1392

[ 345-92-6 ] Synthesis Path-Downstream 1~88

1
[ 345-92-6 ]
[ 363-02-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With hydroxyamino hydrochloride In ethanol Heating;
91.9%	With hydroxylamine; sodium hydroxide In methanol at 40℃; for 0.166667h;
88.5%	With hydroxyamino hydrochloride; sodium hydroxide In ethanol; lithium hydroxide monohydrate Reflux;	3.2. 1.1. General Procedures for Synthesis of Oxime Substrates 2a-2o General procedure: Ketone (0.027 mol) and hydroxylamine hydrochloride (3.0 g, 0.043 mol) were dissolved in EtOH (10 mL) and H2O (20 mL). To the mixture was added NaOH (5.5 g, 0.137 mol). The reaction mixture was heated under reflux and the reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, the reaction mixture was cooled down to room temperature, to the reaction mixture were added concentrated hydrochloric acid (15 mL) and water (100 mL). The solid was filtered off and recrystallized from EtOH, affording the products 2a-2o.

60%	With hydroxyamino hydrochloride In ethanol; lithium hydroxide monohydrate at 100℃; for 4h; Sealed tube;	2. General procedures for the synthesis of oxime substrates 1a-1k General procedure: The solution of the aryl ketones (3 mmol) and hydroxylamine hydrochloride (0.42 g, 6 mmol) in 4 mL H2O and 4 mL EtOH was added in a sealed tube. The mixture was then refluxed for 4 h. An aqueous solution of sodium bicarbonate was added. The mixture was extracted with ethyl acetate and the combined organic phase was washed with the aqueous solution of sodium bicarbonate and brine, dried over anhydrous Na2SO4 and concentrated in vacuo to afford a residue, whcih was purified by a flash column chromatography on silica gel to afford the products 1a-1k.
52%	With hydroxyamino hydrochloride In lithium hydroxide monohydrate; dimethyl sulfoxide Heating;
	With sodium hydroxide; hydroxyamino hydrochloride In ethanol; lithium hydroxide monohydrate for 1h; Heating;
	With sodium hydroxide; hydroxyamino hydrochloride
	With pyridine; hydroxyamino hydrochloride In ethanol for 18h; Reflux;
	Stage #1: 4,4'-Difluorobenzophenone With hydroxyamino hydrochloride In ethanol; lithium hydroxide monohydrate for 5h; Reflux; Stage #2: With sodium hydroxide In ethanol; lithium hydroxide monohydrate
	With hydroxyamino hydrochloride; anhydrous Sodium acetate In ethanol; lithium hydroxide monohydrate Reflux;	2. Synthetic procedure for oxime^[1,2,3] General procedure: To a 100 mL round bottom flask charged with a stir bar, sodium acetate (50.0 mmol) and hydroxylamine hydrochloride (30.0 mmol), was added a solution of the ketone (0.3 M) in ethanol/water (1:3). The reaction mixture was then heated to reflux until all the ketone starting material was consumed as indicated by TLC. After reflux, the reaction was allowed to cool to rt. The crude mixture was obtained after removal of excess ethanol. To the crude mixture was added 20 mL of water. The resulting aqueous solution was extracted with EtOAc (3 × 20 mL). The combined organic layers were then washed with water (2 × 20 mL) and brine (1 × 20 mL), dried over anhydrous MgSO4, filtered and concentrated. The oxime product was used directly in the next step. In certain cases, the oxime product was obtained after flash column chromatography.
	With hydroxyamino hydrochloride; anhydrous Sodium acetate In ethanol; lithium hydroxide monohydrate at 80℃; Inert atmosphere; Schlenk technique;
	With hydroxyamino hydrochloride; anhydrous Sodium acetate In methanol at 75℃;
	With hydroxyamino hydrochloride; anhydrous Sodium acetate In ethanol at 95℃; Inert atmosphere; Glovebox;
	With pyridine; hydroxyamino hydrochloride In ethanol for 10h; Sealed tube; Reflux;

Reference： [1]Zhang; Joseph; Bowen; Flippen-Anderson; Dersch; Rothman; Jacobson; Rice [Journal of Medicinal Chemistry, 2001, vol. 44, # 23, p. 3937 - 3945]
[2]Zhang, Wenwen; Yang, Shiwei; Lin, Qiuyu; Cheng, Heyong; Liu, Jinhua [Journal of Organic Chemistry, 2019, vol. 84, # 2, p. 851 - 859]
[3]Hu, Hongyu; Cai, Xuting; Xu, Zhuying; Yan, Xiaoyang; Zhao, Shengxian [Molecules, 2018, vol. 23, # 7]
[4]Xie, Fukai; Du, Chuan; Pang, Yadong; Lian, Xu; Xue, Chentao; Chen, Yanyu; Wang, Xuefei; Cheng, Maosheng; Guo, Chun; Lin, Bin; Liu, Yongxiang [Tetrahedron Letters, 2016, vol. 57, # 51, p. 5820 - 5824]
[5]Ciccone, Lidia; Nencetti, Susanna; Rossello, Armando; Stura, Enrico Adriano; Orlandini, Elisabetta [Journal of Enzyme Inhibition and Medicinal Chemistry, 2016, vol. 31, p. 40 - 51]
[6]Bradlow; VanderWerf [Journal of the American Chemical Society, 1947, vol. 69, p. 662] Dunlop; Gardner [Journal of the American Chemical Society, 1933, vol. 55, p. 1665] Iris; Mendizabal [1947, vol. 8, p. 63,66][Chem.Abstr., 1948, p. 1920]
[7]Harada; Ohno; Kobayashi; Mukaiyama [Synthesis, 1991, # 12, p. 1216 - 1220]
[8]Jain, Ajay K.; Singh, Prashant; Sahoo [Journal of Physical Organic Chemistry, 1996, vol. 9, # 11, p. 770 - 776]
[9]Gerfaud, Thibaud; Neuville, Luc; Zhu, Jieping [Angewandte Chemie - International Edition, 2009, vol. 48, # 3, p. 572 - 577]
[10]Zhi, Peng; Xi, Zi-Wei; Wang, Dan-Yan; Wang, Wei; Liang, Xue-Zheng; Tao, Fei-Fei; Shen, Run-Pu; Shen, Yong-Miao [New Journal of Chemistry, 2019, vol. 43, # 2, p. 709 - 717]
[11]Xu, Ze-Feng; Zhang, Teng; Hong, Wenjun [Tetrahedron, 2019, vol. 75, # 23, p. 3113 - 3117]
[12]Patra, Tuhin; Mukherjee, Satobhisha; Ma, Jiajia; Strieth-Kalthoff, Felix; Glorius, Frank [Angewandte Chemie - International Edition, 2019, vol. 58, # 31, p. 10514 - 10520][Angew. Chem., 2019, vol. 131, p. 10624 - 10630,7]
[13]Wei, Ziyan; Yu, Shouyun; Zhang, Ai Hua; Zhang, Hao [Organic Letters, 2020, vol. 22, # 18, p. 7315 - 7320]
[14]Chang, Junbiao; Deng, Wei-Qiao; Kong, Lingheng; Li, Xingwei; Liu, Bingxian; Sun, Lincong; Wang, Fen; Zhao, Yanlian [Chemical Communications, 2021, vol. 57, # 67, p. 8268 - 8271]
[15]Kang, Yan-Shang; Liu, Yao-Yao; Lu, Yi; Qu, Yuan-Lu; Sun, Wei-Yin; Zhu, Yue-Lu [Organic Letters, 2022, vol. 24, # 17, p. 3118 - 3122]

2
[ 365-24-2 ]
[ 345-92-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium carbonate; chlorobenzene; 2-dicyclohexylphosphino-1,1'-biphenyl In toluene at 105℃; for 12h;
98%	With potassium carbonate; chlorobenzene In toluene at 105℃; for 12h;
98%	With potassium tetrakis-μ-pyrophosphitodiplatinate(II); tetra-n-butyl-ammonium chloride In dichloromethane; lithium hydroxide monohydrate at 20℃; for 8h; Inert atmosphere; Irradiation;

98%	With ruthenium(III) trichloride hydrate; oxygen; C₂₅H₄₄NO₂PS In 1,2-dichloro-ethane at 23℃; for 24h;
95%	With NBS; anhydrous potassium acetate In dichloromethane; lithium hydroxide monohydrate at 20℃; for 10h; Green chemistry;	General Procedure for the Oxidative Reaction General procedure: A solution of diphenylmethanol (1 mmol), NBS (1.3equiv.), KOAc (1.5 equiv.) H2O (1.5 mL), and CH2Cl2 (0.5mL) was magnetically stirred in 25 mL flask at room temperaturefor 10 h. The reaction mixture was added into water(10 mL), and extracted with EtOAc (3 × 10 mL). The combinedEtOAc extracts were dried over anhydrous MgSO4,filtrated, and then the solvent was removed under reducedpressure. The residue was purified by the flash columnchromatography on silica gel with PE or PE/EtOAc as theeluent to obtain the desired products. The oxidation productswere identified by GC-MS and 1H NMR.
95%	With potassium monopersulfate triple salt; 2-iodo-N-isopropyl-5-methoxybenzamide; tetrabutylammonium hydrogensulfate In nitromethane; lithium hydroxide monohydrate at 25℃; for 9h; Green chemistry;	Typical experimental procedure for oxidation of secondary alcohols 14a-f [7] General procedure: Secondary alcohol 14 (0.50 mmol) was added to a solution of the catalyst (0.15 mmol) and Bu4NHSO4 (170 mg, 0.50mmol) in a mixture of MeNO2 (1.6 mL) and water (0.6 mL), followed by Oxone (768 mg. 1.25 mmol) at room temperature (25 C). After 14 was completely consumed as indicated by TLC, the resulting mixture was diluted with EtOAc and washed with water. The organic layer was then washed with saturated aqueous Na2S2O3 and saturated aqueous NaHCO3, dried over MgSO4; filtered; and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give pure ketone 15 and the catalyst. All ketones 15 were directly identified by comparison with the commercial samples.
94%	With tert.-butylhydroperoxide; vanadium pentoxide In lithium hydroxide monohydrate at 100℃; for 24h;	4.3. Typical experimental procedure for oxidation of alcohols General procedure: To a well-stirred suspension of alcohol (1 mmol) and V2O5 (0.05 mmol) in water (1 mL) was added aq TBHP (70%, 4 mmol). The reaction mixture was heated at reflux until the completion of the reaction (monitored by TLC). The reaction mixture was extracted with ethyl acetate (3×15 mL). The combined organic layer was dried over Na2SO4 and evaporated under vacuum to furnish the crude product, which was purified on a silica gel column using EtOAc and hexane as the solvent mixture. In case of problem in isolating the acid, the solvent was evaporated under vacuum and the crude residue was purified by column chromatography on silica gel (EtOAc/hexane).
93%	With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium carbonate; isocyanuric acid In ethyl acetate at 0 - 10℃; for 6h;	General Procedure for the oxidation of alcohols employing nitroxyl radical / imide / NaOCl in the presence of K₂CO₃. General procedure: To a mixture of the alcohol (3.839 mmol), K2CO3 (2.0 equiv, 7.678 mmol) and cyanuric acid (0.1 equiv, 0.384 mmol) in 20 mL of ethyl acetate were added TEMPO or AZADO (3 mol%, 0.115 mmol) and 12% NaOCl (1.2 equiv, 4.607 mmol, Wako Pure Chemical Industries, Ltd.) at 0-10°C. The mixture was then stirred to complete. The reaction mixture was extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to afford the corresponding product.
93%	With nickel trifluoromethanesulfonate; cyclohexanone; 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 110℃; for 12h; Schlenk technique;
92%	With oxygen In various solvent(s) at 105℃; for 36h;
91%	With dimanganese decacarbonyl In toluene at 120℃; Sealed tube;
90%	With dihydrogen peroxide; glacial acetic acid In lithium hydroxide monohydrate; acetonitrile at 20℃; for 1h;	2.2. General procedure for the catalytic oxidation of secondary alcohols General procedure: In a typical reaction, a MeCN (1 mL) solution of substrate(0.5 mmol), catalyst (0.1 mol% Mn content) and acetic acid (2equiv) was added into a 10 mL flask at room temperature. Then aH2O2 solution (1.5 equiv, diluted from a 30% aqueous solution in0.6 mL of MeCN) was added via a syringe pump over 30 min withstirring at room temperature. The solution was further stirred atroom temperature for 30 min. At this point, nitrobenzene ordecane was added to the mixture as the internal reference (forGC yield). The reaction was quenched with a saturated NaHCO3 aqueous solution, and saturated Na2S2O3 aqueous solution,extracted with ether or dichloromethane, then determined by GCHP-5 capillary column, 30 m 0.32 mm 0.25 mm)and GC-MS analysis or directly loaded on a flash column chromatographyto get pure products.
88%	With sodium trifluoro-methanesulfinate In acetonitrile at 25℃; for 12h; Irradiation; Sealed tube;
85%	With tert.-butylhydroperoxide In lithium hydroxide monohydrate at 100℃; for 24h;	General procedure for the oxidative reaction General procedure: Caution. tert-Butyl hydroperoxide is an exceptionally dangerous chemical that is highly reactive, flammable, and toxic. It is corrosive to skin and mucous membranes and causes respiratory distress when inhaled. A solution of secondary alcohol (1 mmol) and 70% TBHP (6 or 10 equiv.) was stirred at 100 °C for 24 h. The reaction mixture was quenched with the saturated solution of sodium thiosulfate (5 mL) and extracted with dichloromethane (3 x 10 mL). The combined dichloromethane extracts were dried over anhydrous Na2SO4 and filtered, and then the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel with PE or PE/EtOAc as the eluent to obtain the desired products.
78%	With iodine; oxygen In acetonitrile at 20℃; for 7h; Irradiation;
78%	With tert.-butylhydroperoxide; Cu(OAc)₂*H₂O In lithium hydroxide monohydrate at 80℃; for 8h;
75%	With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; tetra-n-butylammonium azide In acetonitrile at 25℃; for 12h; Irradiation;
74%	In neat (no solvent) at 100℃; for 6h;	General Procedures Condition A General procedure: A mixture of thesubstrate (250 μmol), KOH (15.4 mg, 275 μmol) and 10% Ru/C(12.6 mg, 12.5 μmol) was stirred at 100 °C using a test tubeequipped with air balloon. After the corresponding reactiontime, the mixture was filtered through a membrane filter (poresize: 0.2 μm). The catalyst on the filter was washed with H2Oand CH2Cl2 and extracted with CH2Cl2 (5 mL × 3). The combinedorganic layers were dried over Na2SO4 and concentratedin vacuo. The residue was further purified by silica-gel columnchromatography
70%	With tripotassium phosphate tribasic; carbon dioxide In dimethyl sulfoxide at 90℃; for 48h;
56%	With oxygen; HNO₃; 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; lithium hydroxide monohydrate at 20℃; for 18h; Sealed tube;
55%	With Nitrogen dioxide In acetonitrile at 140℃; for 5h; Sealed tube;	2.2. General procedure for the aerobic oxidation of various substrates General procedure: To a dried 45 mL tube equipped with a magnetic stirring, 2 mL acetonitrile, 0.5 mmol substrate and 0.046 mmol NO2 were sequentially added (note: the air in the tube was not removed). Then the reaction tube was sealed and stirred magnetically at a constant-temperature to perform the reaction for 5 h. Once the reaction time was reached, GCanalysis of the mixture provided the GC yields of the products. Then the crude product from another parallel experiment was purified by silicagel chromatography to give the desired product.
36.2%	With dihydrogen peroxide In methanol at -40℃; for 4h; Enzymatic reaction;
	With pyridinium bromochromate; anhydrous sodium perchlorate In glacial acetic acid at 49.9℃; other temperatures; ΔG(excit.), ΔH(excit.), ΔS(excit.);
	With potassium carbonate; chlorobenzene; 2-dicyclohexylphosphino-1,1'-biphenyl In toluene at 105℃; for 12h;
	With triethylamine; pyridinium chlorochromate In dichloromethane at 20℃;
98 %Chromat.	With sodium chlorine monoxide In 1,2-dimethoxyethane; lithium hydroxide monohydrate at 20℃; for 4h;
	With pyridinium chlorochromate In dichloromethane
	With mesoporous silica; pyridinium chlorochromate In dichloromethane at 20℃;	Synthesis of S3 General procedure: To a solution of S2 (6 mmol) in DCM (20 mL), was added silica gel (about 10 g) and PCC (9.0 mmol, 1.5 equiv). Then the mixture was stirred for overnight at room temperature. The mixture was purified by chromatography eluted with DCM to give S3.

Reference： [1]Guram, Anil S.; Bei, Xiaohong; Turner, Howard W. [Organic Letters, 2003, vol. 5, # 14, p. 2485 - 2487]
[2]Current Patent Assignee: FREESLATE, INC. - US6350916, 2002, B1 Location in patent: Example 1
[3]Zhong, Jian-Ji; To, Wai-Pong; Liu, Yungen; Lu, Wei; Che, Chi-Ming [Chemical Science, 2019, vol. 10, # 18, p. 4883 - 4889]
[4]Hu, Rong-Bin; Lam, Ying-Pong; Ng, Wing-Hin; Wong, Chun-Yuen; Yeung, Ying-Yeung [ACS Catalysis, 2021, vol. 11, # 6, p. 3498 - 3506]
[5]Wu, Jianglong; Liu, Yan; Liu, Ping; Gu, Chengzhi [Letters in Organic Chemistry, 2017, vol. 14, # 4, p. 254 - 260]
[6]Yakura, Takayuki; Fujiwara, Tomoya; Yamada, Akihiro; Nambu, Hisanori [Beilstein Journal of Organic Chemistry, 2018, vol. 14, p. 971 - 978]
[7]Location in patent: experimental part Alagiri, Kaliyamoorthy; Prabhu, Kandikere Ramaiah [Tetrahedron, 2011, vol. 67, # 44, p. 8544 - 8551]
[8]Fukuda, Naohiro; Izumi, Minoru; Ikemoto, Tomomi [Tetrahedron Letters, 2015, vol. 56, # 25, p. 3905 - 3908]
[9]Ye, Danfeng; Liu, Zhiyuan; Sessler, Jonathan L.; Lei, Chuanhu [Chemical Communications, 2020, vol. 56, # 79, p. 11811 - 11814]
[10]Guram, Anil; Hagemeyer, Alfred; Lugmair, Claus G.; Turner, Howard W.; Volpe Jr., Anthony F.; Weinberg, W. Henry; Yaccato, Karin [Advanced Synthesis and Catalysis, 2004, vol. 346, # 2-3, p. 215 - 230]
[11]Meng, Shan-Shui; Lin, Li-Rong; Luo, Xiang; Lv, Hao-Jun; Zhao, Jun-Ling; Chan, Albert S. C. [Green Chemistry, 2019, vol. 21, # 22, p. 6187 - 6193]
[12]Lin, Jin; Sun, Wei; Wang, Bingyang; Xia, Chungu [Journal of Catalysis, 2022, vol. 406, p. 87 - 95]
[13]Zhu, Xianjin; Liu, Can; Liu, Yong; Yang, Haijun; Fu, Hua [Chemical Communications, 2020, vol. 56, # 82, p. 12443 - 12446]
[14]Wu, Jianglong; Liu, Yan; Ma, Xiaowei; Liu, Ping; Gu, Chengzhi; Dai, Bin [Synthetic Communications, 2016, vol. 46, # 21, p. 1747 - 1758]
[15]Farhadi, Saeid; Zabardasti, Abedien; Babazadeh, Zaynab [Tetrahedron Letters, 2006, vol. 47, # 50, p. 8953 - 8957]
[16]Wu, Jianglong; Liu, Yan; Ma, Xiaowei; Liu, Ping; Gu, Chengzhi; Dai, Bin [Chinese Journal of Chemistry, 2017, vol. 35, # 9, p. 1391 - 139]
[17]Shee, Maniklal; Singh, N. D. Pradeep [Advanced Synthesis and Catalysis, 2022]
[18]Park, Kwihwan; Jiang, Jing; Yamada, Tsuyoshi; Sajiki, Hironao [Chemical and Pharmaceutical Bulletin, 2021, vol. 69, # 12, p. 1200 - 1205]
[19]Riemer, Daniel; Mandaviya, Bhavdip; Schilling, Waldemar; Götz, Anne Charlotte; Kühl, Torben; Finger, Markus; Das, Shoubhik [ACS Catalysis, 2018, vol. 8, # 4, p. 3030 - 3034]
[20]Arseniyadis, Stellios; Clavier, Louis; Copin, Chloé; Fournier, Jean; Giffard, Jean-François; Jean, Alexandre; Katsina, Tania; Macedo Portela Da Silva, Nayane; Tamion, Rodolphe [Organic process research and development, 2020, vol. 24, # 5, p. 856 - 860]
[21]Ren, Fangping; Tian, Xinzhe; Ren, Yun-Lai; Zhao, Shuang; Wang, Jianji; Zhao, Bo [Catalysis Communications, 2017, vol. 101, p. 98 - 101]
[22]Pan, Wang; Mao, Lijun; Shi, Mingsong; Fu, Yonghong; Jiang, Xiaomin; Feng, Wen; He, Youzhou; Xu, Dingguo; Yuan, Lihua [New Journal of Chemistry, 2018, vol. 42, # 5, p. 3857 - 3866]
[23]Narayanan, N.; Balasubramanian, T. R. [Journal of Chemical Research, Miniprint, 1991, # 12, p. 3052 - 3062]
[24]Bei, Xiaohong; Hagemeyer, Alfred; Volpe, Anthony; Saxton, Robert; Turner, Howard; Guram, Anil S. [Journal of Organic Chemistry, 2004, vol. 69, # 25, p. 8626 - 8633]
[25]Li, Hu; Zhu, Ru-Yi; Shi, Wen-Juan; He, Ke-Han; Shi, Zhang-Jie [Organic Letters, 2012, vol. 14, # 18, p. 4850 - 4853,4]
[26]Fukuda, Naohiro; Kajiwara, Takeshi; Katou, Tomoaki; Majima, Keisuke; Ikemoto, Tomomi [Synlett, 2013, vol. 24, # 11, p. 1438 - 1442]
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3
[ 92-88-6 ]
[ 3236-71-3 ]
[ 345-92-6 ]
Polymer, A/B molar ratio 20/80; Monomer(s): 9,9-bis(4-hydroxyphenyl)fluorene (A); 4,4\-biphenol (B); 4,4\-difluorobenzophenone [ No CAS ]

Reference： [1]Doklady Chemistry,1996,vol. 348,p. 115 - 117

4
[ 3236-71-3 ]
[ 345-92-6 ]
Polymer; Monomer(s): 9,9-bis(4-hydroxyphenyl)fluorene; 4,4\-difluorobenzophenone [ No CAS ]

Reference： [1]Doklady Chemistry,1996,vol. 348,p. 115 - 117

5
[ 1817-74-9 ]
[ 2195-47-3 ]
[ 345-92-6 ]

Reference： [1]Journal of Fluorine Chemistry,1998,vol. 92,p. 127 - 129

6
[ 457-68-1 ]
[ 345-92-6 ]

Yield	Reaction Conditions	Operation in experiment
99%	With pyridine; tert.-butylhydroperoxide In decane; acetonitrile at 80℃; for 24h;
99%	With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; C₁₂H₈Cl₃FeN₂O₄Zr₄; oxygen; sodium nitrite In acetonitrile at 60℃; for 24h;
97%	With oxygen; sodium t-butanolate In dimethyl sulfoxide at 50℃; for 5h; Sealed tube;	2) General procedure for autoxidative oxygenation General procedure: To a predried 5 mL round-bottom flask diarylmethane 1 (0.4 mmol), dry DMSO (1 mL), andt-BuONa (0.8 mmol) were subsequently added as soon as possible. The reaction system wassealed by a rubber septum with a needle connected to an O2 balloon, and then stirred at 50 oC for5 h. During this period, the reaction system suffered complex color changes. Then the reactionmixture was allowed to cool at room temperature, and diluted with 1 mol/L HCl to pH = 6-7,washed with ethyl acetate (20 mL × 3), dried over anhydrous Na2SO4, and filtered to get clearorganic solution. The solvent was removed reduced pressure by a rotary evaporator, and theresulting residue was subjected to column chromatography on silica gel using co-solvent (ethylacetate / petroleum ether = 1/20, v/v) as eluent to give the corresponding diarylketones.

96%	With pyridine; tert.-butylhydroperoxide; air; K⁽¹⁺⁾AuCl₄^(1-)0.5H₂O=K[AuCl₄]*0.5H₂O In decane at 90℃; for 24h;
93%	With pyridine; tert.-butylhydroperoxide; iron(III) chloride at 82℃; for 24h;
93%	With pyridine; tert.-butylhydroperoxide In acetonitrile at 80℃; for 24h;	3 General procedure for the oxidation of benzylic methylenes A mixture of 4,4-diuorodiphenylmethane (178.4 L,1.0 mmol) and P4VPDVB2.5-40%-Fe(III) catalyst (2.0 mol%), pyridine (8.0 L,0.1 mmol), TBHP (5.0-6.0 M in decane, 545.0 L, 3.0 mmol) and 1.0 mL acetonitrile was dissolved in a 25 mL single-necked flask fitted with a reflux condenser. The mixture was heated at 80°C for 24 h under air atmosphere in an oil bath. Then the mixture was cooled to 25°C and centrifuged to get a catalyst and supernatant solution. Then the solution was analyzed by Agilent 7890/5975C-GC/MSD using nitrobenzene as an internal standard. A calibration curve for each reactant and product has been built, which is included in the ESI†. The in situ 1H NMR monitoring of the reaction conversion and yield was performed in the DMSO-d6 solvent, the crude sample of entry 11 in Table 3 was filtered for direct 1H NMR analysis (see ESI†). Furthermore, the products of entries 1 and 7 in Table 2 were isolated through column chromatography and the isolated yields were provided.
93%	With tert.-butylhydroperoxide; C₂₄H₁₈N₆O₃Cu⁽¹⁺⁾I^(1-) In water at 20℃; for 4h;
91%	Stage #1: 4,4'-difluorodiphenylmethane With tetrabutylammonium tetrafluoroborate In dichloromethane at -78℃; Electrolysis; Inert atmosphere; Stage #2: With dimethyl sulfoxide In dichloromethane at -78℃; for 0.0833333h; Inert atmosphere; Stage #3: With triethylamine In dichloromethane at 35℃; for 1h; Inert atmosphere;
90%	With N-Bromosuccinimide; water In chloroform for 3h; Reflux;	Generalprocedure for synthesis of diaryllketones (3a-x) General procedure: In around-bottom flask, diarylmethanes (1.0 mmol), NBS (889.9 mg, 5.0 mmol) andwater (0 or 5.0 mmol) were dissolved in CHCl3 (4.0 mL). After refluxing for 3 h in the air, the reaction mixture was quenched withNa2S2O3·5H2O, cooled to roomtemperature, washed with 5mL CH2Cl2, dried with MgSO4,and filtered to get clear organic solution. The solvent was removed reduced pressure by a rotary evaporator, and the resulting residue was subjected to column chromatography on silica gel using co-solvent(ethyl acetate / petroleum ether, v/v) as eluent to give the corresponding diaryllketones.
88%	With tert.-butylhydroperoxide; copper(II) acetate monohydrate In water at 80℃; for 8h;
84%	With N-hydroxyphthalimide; oxygen In acetonitrile at 80℃; for 12h;
80%	With tert.-butylhydroperoxide In acetonitrile at 70℃;
67%	With oxygen In 1,2-dichloro-benzene at 130℃; for 6h; Schlenk technique;
48%	With cercosporin; oxygen; potassium bromide In methanol at 20℃; Irradiation; Schlenk technique; Green chemistry; chemoselective reaction;
30%	With sodium hypochlorite; tetra(n-butyl)ammonium hydrogensulfate; sodium bromide In hexane at 25℃; for 8h;
89 % Chromat.	With N-hydroxyphthalimide; oxygen; benzaldehyde In acetic acid at 30℃; for 7h;
99 %Chromat.	With pyridine; tert.-butylhydroperoxide; nickel cobalt oxide In acetonitrile at 90℃; for 24h;
	With N-hydroxyphthalimide; oxygen In acetonitrile at 60℃; for 24h;
	With nitric acid for 6h; Reflux;	according to the present invention the preparation method of 4, 4'-difluorobenzophenone, it includes the following preparation steps the above obtained 4, 4'-difluorodiphenyl methane is put into a flask, add quantitative 24% dilute nitric acid and catalyst, warmed to reflux temperature, after that added the drops of measured amount 55% of nitric acid, add about 4h and then finished, after adding the drops carry on reaction for 2h, cool at room temperature to precipitate the crystals, filter, the filtrate is reused, the filter material is re-crystallized from 70% ethanol, dry and then obtained white flake 4,4'-difluorobenzophenone crystals.
93 %Spectr.	With oxygen In dodecane at 120℃; for 10.5h;	2.3. Catalytic aerobic oxidation of alkylarenes General procedure: The oxidation was carried out in a carousel reaction tube to which diphenylmethane (1.0 mmol), Ni2Mn-LDH (0.2 g), dodecane (2 mL) and chlorobenzene (0.5 mmol, used as the internal standard reference) were added. The mixture was then magnetically stirred at 120 under oxygen atmosphere (1 atm). The reaction was sampled periodically andanalyzed through a gas chromatograph (Shimadzu GC-2010AF). Afterthe reaction, the catalyst was separated via filtration, washed with ethyl acetate, dried at 120 for 4 h and introduced into a new reaction torecycle the catalyst. The conversion of the diphenylmethane and the selectivity of benzophenone were calculated using the internal standardmethod according to the GC analysis with no allowance for the background.The turnover frequency (TOF) value was calculated based onthe mol of diphenylmethane converted per hour per mol of Mn on thesurfaces of catalysts. The catalytic oxidations of other substrates wereconducted with similar procedure, and the conversion and selectivitywere calculated using the normalization method. Some of the productswere isolated using flash chromatography analyzed through a NMR spectrometer.
41 %Chromat.	With tert.-butylhydroperoxide; 2Cu⁽²⁺⁾C₃₃H₁₇NO₈^(4-)H₂O*3C₃H₇NO In acetonitrile at 65℃; for 24h;

Reference： [1]Li, Ruilian; Zhao, Jian; Yang, Fengxia; Zhang, Yingchao; Ramella, Daniele; Peng, Yu; Luan, Yi [RSC Advances, 2017, vol. 7, # 81, p. 51142 - 51150]
[2]Shu, Xin; Yu, Ying; Jiang, Yi; Luan, Yi; Ramella, Daniele [Applied Organometallic Chemistry, 2017, vol. 31, # 12]
[3]Li, Jiang-Sheng; Yang, Fan; Yang, Qian; Li, Zhi-Wei; Chen, Guo-Qin; Da, Yu-Dong; Huang, Peng-Mian; Chen, Chao; Zhang, Yuefei; Huang, Ling-Zhi [Synlett, 2017, vol. 28, # 8, p. 994 - 998]
[4]Location in patent: experimental part Li, Huanrong; Li, Zhiping; Shi, Zhangjie [Tetrahedron, 2009, vol. 65, # 9, p. 1856 - 1858]
[5]Nakanishi, Masafumi; Bolm, Carsten [Advanced Synthesis and Catalysis, 2007, vol. 349, # 6, p. 861 - 864]
[6]Fan, Shuang; Luan, Yi; Wang, Jingjing; Gao, Hongyi; Zhang, Xiaowei; Wang, Ge [Journal of Molecular Catalysis A: Chemical, 2015, vol. 404-405, p. 186 - 192]
[7]Wang, Xiaolu; Liu, Mengjia; Wang, Yuqing; Fan, Hongyan; Wu, Jie; Huang, Chao; Hou, Hongwei [Inorganic Chemistry, 2017, vol. 56, # 21, p. 13329 - 13336]
[8]Ashikari, Yosuke; Nokami, Toshiki; Yoshida, Jun-Ichi [Journal of the American Chemical Society, 2011, vol. 133, # 31, p. 11840 - 11843]
[9]He, Chao; Zhang, Xiaohui; Huang, Ruofeng; Pan, Jing; Li, Jiaqiang; Ling, Xuege; Xiong, Yan; Zhu, Xiangming [Tetrahedron Letters, 2014, vol. 55, # 32, p. 4458 - 4462]
[10]Wu, Jianglong; Liu, Yan; Ma, Xiaowei; Liu, Ping; Gu, Chengzhi; Dai, Bin [Chinese Journal of Chemistry, 2017, vol. 35, # 9, p. 1391 - 139]
[11]Liu, Xiangxiang; Luo, Xian-Sheng; Deng, Han-Lin; Fan, Wenhao; Wang, Shuifeng; Yang, Chaojie; Sun, Xiao-Yu; Chen, Shi-Lu; Huang, Mu-Hua [Chemistry of Materials, 2019, vol. 31, # 15, p. 5421 - 5430]
[12]Krishna; Kumari, Shweta; Sharma, Sunil K.; Yadav, Deepak [Applied Catalysis A: General, 2020, vol. 601]
[13]Nakai, Satoru; Uematsu, Tsubasa; Ogasawara, Yoshiyuki; Suzuki, Kosuke; Yamaguchi, Kazuya; Mizuno, Noritaka [ChemCatChem, 2018, vol. 10, # 5, p. 1096 - 1106]
[14]Li, Jia; Bao, Wenhao; Tang, Zhaocheng; Guo, Baodang; Zhang, Shiwei; Liu, Haili; Huang, Shuping; Zhang, Yan; Rao, Yijian [Green Chemistry, 2019, vol. 21, # 22, p. 6073 - 6081]
[15]Clark; Grigoropoulou; Scott [Synthetic Communications, 2000, vol. 30, # 20, p. 3731 - 3735]
[16]De Vondervoort, Lizette Schmieder-van; Bouttemy, Sabine; Heu, Ferdinand; Weissenboeck, Kurt; Alsters, Paul L. [European Journal of Organic Chemistry, 2003, # 3, p. 578 - 586]
[17]Wang, Jingjing; Fan, Shuang; Luan, Yi; Tang, Jia; Jin, Zhaokui; Yang, Mu; Lu, Yunfeng [RSC Advances, 2015, vol. 5, # 4, p. 2405 - 2410]
[18]Fan, Shuang; Dong, Wenjun; Huang, Xiubing; Gao, Hongyi; Wang, Jingjing; Jin, Zhaokui; Tang, Jia; Wang, Ge [ACS Catalysis, 2017, vol. 7, # 1, p. 243 - 249]
[19]Current Patent Assignee: WEIXUN CHEMICAL NANJING - CN106008182, 2016, A Location in patent: Paragraph 0006
[20]Wang, Anwei; Zhou, WeiYou; Sun, Zhonghua; Zhang, Zhong; Zhang, Zhihui; He, MingYang; Chen, Qun [Molecular catalysis, 2021, vol. 499]
[21]Carter, Joseph H.; Day, Sarah J.; Han, Xue; Kang, Xinchen; Kimberley, Louis; Li, Jiangnan; McInnes, Eric J. L.; Schröder, Martin; Sheveleva, Alena M.; Smith, Gemma L.; Tang, Chiu C.; Tuna, Floriana; Yang, Sihai [Angewandte Chemie - International Edition, 2021, vol. 60, # 28, p. 15243 - 15247][Angew. Chem., 2021, vol. 133, # 28, p. 15371 - 15375]

7
[ 1826-67-1 ]
[ 345-92-6 ]
[ 99734-06-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;
85%	In tetrahydrofuran; diethyl ether for 5h; Heating;
72%	In tetrahydrofuran at -78℃; Inert atmosphere;	1,1-bis(4-fluorophenyl)prop-2-en-1-ol To a solution of ketone (1g, 5mmol) in THF (40ml) was added 1 M vinylmagnesium bromide (7.5mL) at -78 °C under Ar. After stirring for 3 h, the solution was warmed to room temperature. The reaction was quenched with ice (15g), and the mixture was diluted with a sat. NH4Cl solution. The THF was evaporated, the crude mixture was extracted with Et2O (3x50 mL), and the organic layer was washed with NaCl (2x30 ml), dried (MgSO4), Filtration, evaporation in vacuo, and purification by flash chromatography (PE:EtOAc = 20:1-10:1) afforded 844mg (72%) as a liquid. 1H NMR (400 MHz, CDCl3) δ 7.33 (dd, J = 5.2, 8.0 Hz, 4H), 7.01 (t, J = 8.4 Hz, 4H), 6.44 (dd, J = 10.4, 16.8 Hz, 1H), 5.26-5.34 (m, 2H), 2.26 (brs, 1H).

	In tetrahydrofuran Inert atmosphere;
	In tetrahydrofuran at 0 - 25℃; for 0.333333h; Inert atmosphere;
	In tetrahydrofuran at 20℃; Inert atmosphere; Cooling with ice;	4.2 General procedure for preparation of cyclic, acyclic allylic alcohols, 40 furan-2-yl(phenyl)methanol and 41 phenyl(thiophen-2-yl)methanol [21] General procedure: To a two-necked flask under argon atmosphere loaded with a solution of ketone (5mmol) in anhydrous THF (5mL) then under vigorous stirring Grignard reagent (1.0M in THF, 5.5mL, 5.5mmol, 1.1 equiv.) was dropwise added via syringe in ice-bath. The mixture was stirred for 0.5h in ice bath, then warmed to room temperature and stirred for 2-5h. After detected by TLC, aqueous NH4Cl (6mL) was added to quench the reaction, then the mixture was extracted with EtOAc (5mL×3). The combined organic layers were dried over anhydrous magnesium. The solvent was removed in vacuo by ratory evaporator. And the crude was purified by chromatography on silica gel to obtain desired allylic alcohols.
	In tetrahydrofuran at 0 - 25℃; for 6h; Inert atmosphere;
	In tetrahydrofuran at 0 - 20℃; Inert atmosphere;
	In tetrahydrofuran at 60℃; Inert atmosphere;	Synthesis of 1a-1u General procedure: To a solution of S3 (5.0 mmol) in THF (5 mL) was added allylmagenesium bromide (7.5 mmol) in THF at room temperature under argon atmosphere . Then the mixture was stirred for overnight at 60 0C and monitored by TLC. Quenched with water (20 mL), the mixture was extracted with EA. Evaporation of the organic phase afforded a crude product, which could be purified by chromatography (PE:EA=10:1) to give the product 1a-1u.
	In tetrahydrofuran at 0 - 20℃; Inert atmosphere;

Reference： [1]Zhang, Zhen; Li, Cheng; Wang, Shao-Hua; Zhang, Fu-Min; Han, Xue; Tu, Yong-Qiang; Zhang, Xiao-Ming [Organic and Biomolecular Chemistry, 2017, vol. 15, # 15, p. 3239 - 3247]
[2]Botteghi, Carlo; Marchetti, Mauro; Paganelli, Stefano; Persi-Paoli, Francesco [Tetrahedron, 2001, vol. 57, # 8, p. 1631 - 1637]
[3]Chen, Gang; Xia, Hongguang; Cai, Yu; Ma, Dawei; Yuan, Junying; Yuan, Chengye [Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 1, p. 234 - 239]
[4]Mo, Xiaobin; Hall, Dennis G. [Journal of the American Chemical Society, 2016, vol. 138, # 34, p. 10762 - 10765]
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[7]Zhang, Dong-Yang; Zhang, Ying; Wu, Hua; Gong, Liu-Zhu [Angewandte Chemie - International Edition, 2019, vol. 58, # 22, p. 7450 - 7453][Angew. Chem., 2019, vol. 131, # 22, p. 7528 - 7531,4]
[8]Guan, Zhipeng; Wang, Huamin; Huang, Yange; Wang, Yunkun; Wang, Shengchun; Lei, Aiwen [Organic Letters, 2019, vol. 21, # 12, p. 4619 - 4622]
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8
[ 56-23-5 ]
[ 462-06-6 ]
[ 342-25-6 ]
[ 345-92-6 ]