Nickel-Catalyzed C-S Reductive Cross-Coupling of Alkyl Halides with Arylthiosilanes toward Alkyl Aryl Thioethers

A nickel-catalyzed C-S reductive cross-coupling of alkyl halides with arylthiosilanes for producing alkyl aryl thioethers is developed. This reaction is initiated by umpolung transformations of arylthiosilanes followed by C-S reductive cross coupling with alkyl halides to manage an electrophilic alkyl group onto the electrophilic sulfur atom and then construct a C(sp(3))-S bond, and features exquisite chemoselectivity, excellent tolerance of diverse functional groups, and wide applications for late-stage modification of biologically relevant molecules.

Automated summary

A nickel-catalyzed C-S reductive cross-coupling reaction has been developed for the synthesis of alkyl aryl thioethers from alkyl halides and arylthiosilanes. This reaction involves umpolung transformations of arylthiosilanes followed by C-S reductive cross-coupling with alkyl halides to form C(sp(3))-S bond. It exhibits exquisite chemoselectivity, excellent tolerance of diverse functional groups, and wide applications for the late-stage modification of biologically relevant molecules.