Copper-catalyzed trifluoromethylation of arylsulfinate salts using an electrophilic trifluoromethylation reagent

被引：32

作者：

Lin, Xiaoxi ^{[1
,2
]}

Wang, Guimei ^{[1
]}

Li, Huaifeng ^{[3
,4
]}

Huang, Yuanyuan ^{[1
]}

He, Weiming ^{[1
]}

Ye, Dandan ^{[1
]}

Huang, Kuo-Wei ^{[3
,4
]}

Yuan, Yaofeng ^{[1
]}

Weng, Zhiqiang ^{[1
,2
]}

机构：

[1] Fuzhou Univ, Dept Chem, Fuzhou 350108, Fujian, Peoples R China

[2] Chinese Acad Sci, Fujian Inst Res Struct Matter, State Key Lab Struct Chem, Fuzhou 350002, Fujian, Peoples R China

[3] KAUST, Div Phys Sci & Engn, Thuwal 239556900, Saudi Arabia

[4] KAUST Catalysis Ctr, Thuwal 239556900, Saudi Arabia

来源：

TETRAHEDRON | 2013年 / 69卷 / 12期

基金：

中国国家自然科学基金;

关键词：

Copper catalyst; Electrophilic trifluoromethylation reaction; Arykrifluoromethylsulphones; MEDIATED REDUCTIVE TRIFLUOROMETHYLATION; OXIDATIVE TRIFLUOROMETHYLATION; 2-PHOTON ABSORPTION; TERMINAL ALKYNES; BORONIC ACIDS; ARYL IODIDES; PERFLUOROALKYLATION; PALLADIUM; ARENES; FLUORINATION;

D O I：

10.1016/j.tet.2013.01.041

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A copper-catalyzed method for the trifluoromethylation of arylsulfinates with Togni's reagent has been developed, affording aryltrifluoromethylsulfones in moderate to good yields. A wide range of functional groups in arylsulfinates are compatible with the reaction conditions. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：2628 / 2632

页数：5

共 80 条

[1] Aryl-CF3 Bond-Forming Reductive Elimination from Palladium(IV) [J].

Ball, Nicholas D. ;

Kampf, Jeff W. ;

Sanford, Melanie S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (09) :2878-+

[2] A new class of 3′-sulfonyl BINAPHOS ligands:: Modulation of activity and selectivity in asymmetric palladium-catalysed hydrophosphorylation of styrene [J].

Barta, Katalin ;

Francio, Giancarlo ;

Leitner, Walter ;

Lloyd-Jones, Guy C. ;

Shepperson, Ian R. .

ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (13) :2013-2023

[3] PREPARATION AND FLUORINATION OF ARYLTRIFLUOROMETHYLSULPHONES [J].

BEAUMONT, AJ ;

CLARK, JH .

JOURNAL OF FLUORINE CHEMISTRY, 1991, 52 (03) :295-300

[4] Tetrahydropyridine-4-carboxamides as novel, potent transient receptor potential vanilloid 1 (TRPV1) antagonists [J].

Brown, Brian S. ;

Keddy, Ryan ;

Zheng, Guo Zhu ;

Schmidt, Robert G. ;

Koenig, John R. ;

McDonald, Heath A. ;

Bianchi, Bruce R. ;

Honore, Prisca ;

Jarvis, Michael F. ;

Surowy, Carol S. ;

Polakowski, James S. ;

Marsh, Kennan C. ;

Faltynek, Connie R. ;

Lee, Chih-Hung .

BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (18) :8516-8525

[5] DIRECT TRIFLUOROMETHYLTHIOLATION OF ARYL HALIDES USING METHYL FLUOROSULFONYLDIFLUOROACETATE AND SULFUR [J].

CHEN, QY ;

DUAN, JX .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (11) :918-919

[6] The Palladium-Catalyzed Trifluoromethylation of Aryl Chlorides [J].

Cho, Eun Jin ;

Senecal, Todd D. ;

Kinzel, Tom ;

Zhang, Yong ;

Watson, Donald A. ;

Buchwald, Stephen L. .

SCIENCE, 2010, 328 (5986) :1679-1681

[7] Copper-Catalyzed Direct C-H Oxidative Trifluoromethylation of Heteroarenes [J].

Chu, Lingling ;

Qing, Feng-Ling .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (02) :1298-1304

[8] Copper-Mediated Oxidative Trifluoromethylation of Boronic Acids [J].

Chu, Lingling ;

Qing, Feng-Ling .

ORGANIC LETTERS, 2010, 12 (21) :5060-5063

[9] REACTION OF TRIFLIC ANHYDRIDE WITH GRIGNARD-REAGENTS - OXIDIZING PROPERTIES OF TRIFLIC ANHYDRIDE [J].

CREARY, X .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (13) :2727-2729

[10] Active trifluoromethylating agents from well-defined copper(I)-CF3 complexes [J].

Dubinina, Galyna G. ;

Furutachi, Hideki ;

Vicic, David A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (27) :8600-+

← 1 2 3 4 5 6 7 8 →