Tri- and di-fluoroethylation of alkenes by visible light photoredox catalysis

被引：16

作者：

Pan, Xiao-Yang ^{[1
,2
,3
]}

Zhao, Yue ^{[1
,2
,3
]}

Qu, Hong-An ^{[4
]}

Lin, Jin-Hong ^{[3
]}

Hang, Xiao-Chun ^{[1
,2
]}

Xiao, Ji-Chang ^{[3
]}

机构：

[1] Nanjing Tech Univ NanjingTech, KLOFE, 30 South Puzhu Rd, Nanjing 211800, Jiangsu, Peoples R China

[2] Nanjing Tech Univ NanjingTech, Inst Adv Mat, 30 South Puzhu Rd, Nanjing 211800, Jiangsu, Peoples R China

[3] Chinese Acad Sci, Univ Chinese Acad Sci, Shanghai Inst Organ, Key Lab Organofluorine Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China

[4] Shandong NHU Amino Acid Co Ltd, Xinchang, Zhejiang, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2018年 / 5卷 / 09期

关键词：

C-H TRIFLUOROETHYLATION; ARYLBORONIC ACIDS; CARBONYL-COMPOUNDS; TERMINAL ALKYNES; 2,2,2-TRIFLUOROETHYLATION; DIFLUOROCARBENE; TRIFLUOROMETHYLATION; DIFLUOROMETHYLATION; OXYTRIFLUOROMETHYLATION; PHARMACEUTICALS;

D O I：

10.1039/c8qo00082d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The tri- and di-fluoroethylation of alkenes with sulfonium salts, (Ph2S+CH2RF TfO-) (R-F = CF3 or HCF2), by visible light photoredox catalysis to give tri-/di-fluoroethyl alkenes or methoxytri-/di-fluoroethylation products are described. It was found that varying the reaction solvent led to changes in the reaction path.

引用

页码：1452 / 1456

页数：5

共 55 条

[31] Metal-Catalyzed Direct Difluoromethylation Reactions [J].

Rong, Jian ;

Ni, Chuanfa ;

Hu, Jinbo .

ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (02) :139-152

[32] Synthesis of 3-Fluoropyridines via Photoredox-Mediated Coupling of α,α-Difluoro-β-iodoketones with Silyl Enol Ethers [J].

Scherbinina, Sofya I. ;

Fedorov, Oleg V. ;

Levin, Vitalij V. ;

Kokorekin, Vladimir A. ;

Struchkova, Marina I. ;

Dilman, Alexander D. .

JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (24) :12967-12974

[33] Aromatic Trifluoromethylation with Metal Complexes [J].

Tomashenko, Olesya A. ;

Grushin, Vladimir V. .

CHEMICAL REVIEWS, 2011, 111 (08) :4475-4521

[34] Photoredox-Catalyzed Stereoselective Conversion of Alkynes into Tetrasubstituted Trifluoromethylated Alkenes [J].

Tomita, Ren ;

Koike, Takashi ;

Akita, Munetaka .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (44) :12923-12927

[35] Mild and Efficient Palladium-Catalyzed Direct Trifluoroethylation of Aromatic Systems by C-H Activation [J].

Toth, Balazs L. ;

Kovacs, Szabolcs ;

Salyi, Gergo ;

Novak, Zoltan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (06) :1988-1992

[36] Fluorine in Pharmaceutical Industry: Fluorine-Containing Drugs Introduced to the Market in the Last Decade (2001-2011) [J].

Wang, Jiang ;

Sanchez-Rosello, Maria ;

Luis Acena, Jose ;

del Pozo, Carlos ;

Sorochinsky, Alexander E. ;

Fustero, Santos ;

Soloshonok, Vadim A. ;

Liu, Hong .

CHEMICAL REVIEWS, 2014, 114 (04) :2432-2506

[37] Visible-Light-Driven, Radical-Triggered Tandem Cyclization of o-Hydroxyaryl Enaminones: Facile Access to 3-CF2 /CF3-Containing Chromones [J].

Xiang, Haoyue ;

Zhao, Qinglan ;

Tang, Zhenyu ;

Xiao, Junan ;

Xia, Pengju ;

Wang, Chaoming ;

Yang, Chunhao ;

Chen, Xiaoqing ;

Yang, Hua .

ORGANIC LETTERS, 2017, 19 (01) :146-149

[38] Nickel-catalyzed direct C-H trifluoroethylation of heteroarenes with trifluoroethyl iodide [J].

Yan, Sheng-Yi ;

Zhang, Zhuo-Zhuo ;

Shi, Bing-Feng .

CHEMICAL COMMUNICATIONS, 2017, 53 (74) :10287-10290

[39] Pd-catalyzed divergent trifluoroethylation and arylation of arylboronic acids by aryl( 2,2,2-trifluoroethyl)iodonium triflates [J].

Yang, Jing ;

Han, Qiu-Yan ;

Zhao, Cheng-Long ;

Dong, Tao ;

Hou, Zhi-Yuan ;

Qin, Hua-Li ;

Zhang, Cheng-Pan .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (32) :7654-7658

[40] Three-component Oxytrifluoromethylation of Alkenes: Highly Efficient and Regioselective Difunctionalization of C=C Bonds Mediated by Photoredox Catalysts [J].

Yasu, Yusuke ;

Koike, Takashi ;

Akita, Munetaka .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (38) :9567-9571

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