Electrochemical Oxidative 1,2-Dithiocyanation: Access to Functionalized Alkenes and Alkynes

J Org Chem. 2024 Jun 7;89(11):8064-8075. doi: 10.1021/acs.joc.4c00707. Epub 2024 May 17.

Abstract

Reported herein is the 1,2-dithiocyanation of alkenes and alkynes via an efficient and facile electrochemical method. This approach not only showed a broad substrate scope and good functional-group compatibility but also avoided stoichiometric oxidants. Different from previous reports, various internal alkynes could be tolerated to provide tetra-substituted alkenes. Further gram-scale-up experiments and synthetic transformation demonstrated a potential application in organic synthesis. This process underwent a radical pathway, as evidenced by our mechanistic studies.