文献类型：期刊文献

英文题名：Catalyst-free chemoselective conjugate addition and reduction of α,β-unsaturated carbonyl compounds via a controllable boration/protodeboronation cascade pathway

作者：Huang, Xi[1];Hu, Junjie[1];Wu, Mengying[1];Wang, Jiayi[1];Peng, Yanqing[1];Song, Gonghua[1]

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

年份：2018

卷号：20

期号：1

起止页码：255

外文期刊名：GREEN CHEMISTRY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000419060600024)，CCR-EXPANDED(收录号:WOS:000419060600024)】；

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

语种：英文

摘要：A novel, efficient transition-metal-free and controllable boration/protodeboronation strategy has been developed for the chemoselective conjugate addition and 1,4-reduction of alpha,beta-unsaturated carbonyl compounds. Without any metal-catalyst or base, a series of beta-boration products of alpha,beta-unsaturated carbonyl compounds was easily obtained in moderate to excellent yields in a mixed solvent of ethanol and water. The presence of a catalytic amount of Cs2CO3 can effectively induce further protodeboronation reaction towards 1,4-reduction products at higher reaction temperature. Therefore, by slightly changing the reaction conditions, the boration or reduction products of alpha,beta-unsaturated carbonyl compounds can be controllably obtained. Mechanistic studies revealed that Cs2CO3 played the key role in activating the protodeboronation step. This transition-metal-catalyst-free and product controllable method provides a useful and eco-friendly tool for the highly chemoselective preparation of the beta-boration products and 1,4-reduction products of alpha,beta-unsaturated carbonyl compounds.