Palladium-Catalyzed Trifluoromethylthiolation of Aryl C-H Bonds

被引：187
作者：
Xu, Chunfa [1 ]
Shen, Qilong [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China
来源：
ORGANIC LETTERS | 2014年 / 16卷 / 07期
基金：
中国国家自然科学基金;
关键词：
PD(II)-CATALYZED ORTHO-TRIFLUOROMETHYLATION; OXIDATIVE TRIFLUOROMETHYLTHIOLATION; BORONIC ACIDS; CONVENIENT SYNTHESIS; FLUORINATION; ARENES; PERFLUOROALKYLATION; COMPLEXES; REACTIVITY; CONSTRUCTION;
D O I：
10.1021/ol5006533
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A method for monotrifluoromethylthiolation of arenes via palladium-catalyzed directed C-H bond activation was described. The reaction was compatible with a variety of functional groups. Initial mechanistic studies disclosed that the turnover limiting step of the catalytic cycle did not involve C-H activation.
引用
收藏
页码：2046 / 2049
页数：4
相关论文
共 77 条
[1]  
[Anonymous], 1982, BIOMEDICAL ASPESTS F
[2]  
[Anonymous], 1967, CHEM ENG NEWS, V45, P44
[3]   Electrophilic Trifluoromethanesulfanylation of Organometallic Species with Trifluoromethanesulfanamides [J].
Baert, Francois ;
Colomb, Julie ;
Billard, Thierry .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (41) :10382-10385
[4]   Synthesis and Reactivity of a Mono-σ-Aryl Palladium(IV) Fluoride Complex [J].
Ball, Nicholas D. ;
Sanford, Melanie S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (11) :3796-+
[5]  
Becker A., 1996, Inventory of Industrial Fluoro-Biochemicals
[6]   Synthetic uses of thio- and selenoesters of trifluoromethylated acids. 1. Preparation of trifluoromethyl sulfides and selenides [J].
Billard, T ;
Roques, N ;
Langlois, BR .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (11) :3813-3820
[7]   A new simple access to trifluoromethyl thioethers or selenoethers from trifluoromethyl trimethylsilane and disulfides or diselenides [J].
Billard, T ;
Langlois, BR .
TETRAHEDRON LETTERS, 1996, 37 (38) :6865-6868
[8]   Aromatic and heterocyclic perfluoroalkyl sulfides. Methods of preparation [J].
Boiko, Vladimir N. .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2010, 6 :880-921
[9]  
BOIKO VN, 1977, ZH ORG KHIM+, V13, P1057
[10]  
Byers P K, 1986, J. Chem. Soc. Chem. Commun., V1722
12345678