Boron-promoted reductive deoxygenation coupling reaction of sulfonyl chlorides for the C(sp3)-S bond construction

Herein, we report a borane-promoted reductive deoxygenation coupling reaction to synthesize sulfides. This reaction features excellent functional group compatibility, high efficiency, broad substrate scope, and application in late-stage functionalization of biomolecules. Preliminary mechanistic studies suggest di-aryl sulfides are the intermediates of this reaction. Moreover, the real active aryl sulfide anions may be generated in situ with the aid of B(2)pin(2) and react with alkyl tosylates through a concerted S(N)2 pathway. (c) 2022 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.

Automated summary

A borane-promoted reductive deoxygenation coupling reaction for synthesizing sulfides is reported. The reaction shows excellent substrate scope and high efficiency, making it suitable for late-stage functionalization of biomolecules.