Copper-Catalyzed Oxidative Trifluoromethylthiolation of Aryl Boronic Acids with TMSCF3 and Elemental Sulfur

被引：289

作者：

Chen, Chao ^{[1
]}

Xie, Yan ^{[1
]}

Chu, Lingling ^{[1
]}

Wang, Ruo-Wen ^{[1
]}

Zhang, Xingang ^{[1
]}

Qing, Feng-Ling ^{[1
,2
]}

机构：

[1] Chinese Acad Sci, Key Lab Organofluorine Chem, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China

[2] Donghua Univ, Coll Chem Chem Engn & Biotechnol, Shanghai 201620, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 10期

基金：

中国国家自然科学基金;

关键词：

aryl boronic acids; copper catalysis; oxidative coupling; sulfur; trifluoromethylthiolation; MEDIATED TRIFLUOROMETHYLATION; BOND-FORMATION; NUCLEOPHILIC TRIFLUOROMETHYLATION; SELECTIVE TRIFLUOROMETHYLATION; REDUCTIVE ELIMINATION; CONVENIENT SYNTHESIS; MEDICINAL CHEMISTRY; FLUORINATED ETHERS; ARYLBORONIC ACIDS; ROOM-TEMPERATURE;

D O I：

10.1002/anie.201108663

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Fluorinated functionality: The copper-catalyzed oxidative trifluoromethylthiolation of aryl boronic acids with TMSCF 3 and elemental sulfur at room temperature is described for the first time. This reaction provides a concise and efficient method for the synthesis of aryl trifluoromethyl thioethers (ArSCF 3) under mild conditions. Phen=Phenanthroline. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：2492 / 2495

页数：4

共 93 条

[51] Fluorine in pharmaceuticals:: Looking beyond intuition [J].

Mueller, Klaus ;

Faeh, Christoph ;

Diederich, Francois .

SCIENCE, 2007, 317 (5846) :1881-1886

[52] Aromatic trifluoromethylation catalytic in copper [J].

Oishi, Masahiro ;

Kondo, Hideaki ;

Amii, Hideki .

CHEMICAL COMMUNICATIONS, 2009, (14) :1909-1911

[53] Nucleophilic perfluoroalkylation of aldehydes, ketones, imines, disulfides, and diselenides [J].

Pooput, C ;

Dolbier, WR ;

Médebielle, M .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (09) :3564-3568

[54] A new and efficient method for the synthesis of trifluoromethylthio- and selenoethers [J].

Pooput, C ;

Medebielle, M ;

Dolbier, WR .

ORGANIC LETTERS, 2004, 6 (02) :301-303

[55] Copper-Catalyzed Arylation of 1H-Perfluoroalkanes [J].

Popov, Ilya ;

Lindeman, Sergey ;

Daugulis, Olafs .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (24) :9286-9289

[56] DIRECT AND CONVENIENT PREPARATION OF LITHIUM PHENYLTHIO(ALKYL)CUPRATE REAGENTS [J].

POSNER, GH ;

BRUNELLE, DJ ;

SINOWAY, L .

SYNTHESIS-STUTTGART, 1974, (09) :662-663

[57] Alkoxide-and hydroxide-induced nucleophilic trifluoromethylation using trifluoromethyl sulfone or sulfoxide [J].

Prakash, GKS ;

Hu, JB ;

Olah, GA .

ORGANIC LETTERS, 2003, 5 (18) :3253-3256

[58] Fluorine in medicinal chemistry [J].

Purser, Sophie ;

Moore, Peter R. ;

Swallow, Steve ;

Gouverneur, Veronique .

CHEMICAL SOCIETY REVIEWS, 2008, 37 (02) :320-330

[59] A convenient synthesis of trifluoromethyl aryl sulfides [J].

QuicletSire, B ;

Saicic, RN ;

Zard, SZ .

TETRAHEDRON LETTERS, 1996, 37 (50) :9057-9058

[60] TRIFLUOROMETHYLTHIOCOPPER - REAGENT FOR INTRODUCTION OF TRIFLUOROMETHYLTHIO GROUP INTO AROMATIC NUCLEI [J].

REMY, DC ;

RITTLE, KE ;

HUNT, CA ;

FREEDMAN, MB .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (09) :1644-1646

← 1 2 3 4 5 6 7 8 9 10 →