Cuprate ion-pair catalyzed conjugate borylation of vinyl sulfones in a biphasic system

Siyu Jiang; Yicen Ge; Ai Zhang; Silong Hu; Tao Jin; Jian Chen; Huangfeng Zhang; Yao Qin; Xiaoyan Ma; Jinghua Tang; Jinyu Liu

doi:10.1039/D5OB00242G

Cuprate ion-pair catalyzed conjugate borylation of vinyl sulfones in a biphasic system†

Siyu Jiang,^a Yicen Ge,

*^a Ai Zhang,^a Silong Hu,^a Tao Jin,^a Jian Chen,^a Huangfeng Zhang,^a Yao Qin,^a Xiaoyan Ma,

^a Jinghua Tang^a and Jinyu Liu

^a

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* Corresponding authors

^a College of Materials, Chemistry and Chemical Engineering, Chengdu University of Technology, Chengdu, Sichuan 610059, China
E-mail: geyicen@cdut.edu.cn

Abstract

Herein we report the conjugate borylation of vinyl sulfones mediated by ion pairing, which enables the efficient synthesis of β-sulfonyl alcohols bearing diverse functionalities in 13–98% yields. Further mechanistic investigations suggest the formation of anionic boryl-copper intermediates that kinetically accelerate reactant transfer across phases and provide enhanced boryl nucleophilicity.

Organic & Biomolecular Chemistry

Cuprate ion-pair catalyzed conjugate borylation of vinyl sulfones in a biphasic system†

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