Difluoromethylthiolation of Phenols and Related Compounds with a HF2CSO2Na/Ph2PCl/Me3SiCl System

被引：52

作者：

Huang, Zhongyan ^{[1
]}

Matsubara, Okiya ^{[1
]}

Jia, Shichong ^{[1
]}

Tokunaga, Etsuko ^{[1
]}

Shibata, Norio ^{[1
]}

机构：

[1] Nagoya Inst Technol, Dept Nanopharmaceut Sci, Showa Ku, Nagoya, Aichi 4668555, Japan

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 04期

关键词：

HYPERVALENT IODONIUM YLIDE; COPPER-CATALYZED TRIFLUOROMETHYLTHIOLATION; METHIONINE GAMMA-LYASE; ARYL BORONIC ACIDS; OXIDATIVE TRIFLUOROMETHYLTHIOLATION; ELECTROPHILIC TRIFLUOROMETHYLTHIOLATION; MEDIATED TRIFLUOROMETHYLTHIOLATION; N-TRIFLUOROMETHYLTHIOLATION; TERMINAL ALKYNES; IODINE REAGENT;

D O I：

10.1021/acs.orglett.7b00113

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel HF2CSO2Na/Ph2PCl/Me3SiCl system is disclosed for the late-stage direct difluoromethylthiolation of C-sp2 and C-sp3 nudeophiles. Difluoromethylthiolation of phenols and naphthols proceeded nicely under this system to regioselectively provide corresponding SCF2H compounds in good yields. Other substrates such as indoles, pyrroles, pyrazoles, enamines, ketones, and beta-keto esters were also transformed to corresponding SCF2H products in good yields. The late-stage direct difluoromethylthiolation of a number of natural products and pharmaceutically attractive molecules was also achieved.

引用

页码：934 / 937

页数：4