Bromide-Catalyzed Electrochemical Csp3-H Oxidation of Acetonitrile: Stereoselective Synthesis of Heteroaryl Vinyl Sulfides

An electrochemical oxidative C-H/S-H cross-coupling reaction between acetonitrile and heteroaryl thiols has been developed. Me4NBr is employed as a redox catalyst to oxidize both the Csp(3)-H of acetonitrile and S-H of heteroaryl thiols. Heteroaryl vinyl sulfides were afforded under metal-free and oxidant-free reaction conditions in good yields and stereoselectivities with excellent functional group tolerance. The synthetic applicability of the electrochemical method was further highlighted by its easy scalability.

Automated summary

An electrochemical oxidative C-H/S-H cross-coupling reaction has been developed for the synthesis of heteroaryl vinyl sulfides. With acetonitrile and heteroaryl thiols as substrates, the reaction proceeds under metal-free and oxidant-free conditions, leading to high yields and stereoselectivities with excellent functional group tolerance. The synthetic applicability of this electrochemical method has been demonstrated through its easy scalability.