文献类型：期刊文献

英文题名：Catalyst-free chemoselective α-sulfenylation/β-thiolation for α,β-unsaturated carbonyl compounds

作者：Huang, Xi[1];Li, Juan[1];Li, Xiang[1];Wang, Jiayi[1];Peng, Yanqing[1];Song, Gonghua[1]

机构：[1]East China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab Chem Biol, Shanghai 200237, Peoples R China

年份：2019

卷号：9

期号：45

起止页码：26419

外文期刊名：RSC ADVANCES

收录：;EI(收录号：20193707428685);WOS:【SCI-EXPANDED(收录号:WOS:000483541000050)】；

基金：Financial supports for this study from National Natural Science Foundation of China (Grant No. 21572060) and National Key Research and Development Plan (Grant No. 2017YFD0200504) are gratefully acknowledged.

语种：英文

外文关键词：Transition metals - Carbonyl compounds - Chemical reactions - Unsaturated compounds - Catalysts

摘要：A novel, efficient, catalyst-free and product-controllable strategy has been developed for the chemoselective alpha-sulfenylation/beta-thiolation of alpha,beta-unsaturated carbonyl compounds. An aromatic sulfur group could be chemoselectively introduced at alpha- or beta-position of carbonyls with different sulfur reagents under slightly changed reaction conditions. A series of desired products were obtained in moderate to excellent yields. Mechanistic studies revealed that B(2)pin(2) played the key role in activating the transformation towards the beta-thiolation of alpha,beta-unsaturated carbonyl compounds. This transition-metal-catalyst-free method provides a convenient and efficient tool for the highly chemoselective preparation of alpha-thiolation or beta-sulfenylation products of alpha,beta-unsaturated carbonyl compounds.