Metal-free three-component amino- and carbotrideuteromethylthiolation of alkenes in water

Abstract

A metal-free three-component amino- and carbotrideuteromethylthiolation of diverse alkenes in water is developed, providing concise avenues for the preparation of β-functional trideuteromethyl sulfides. Preliminary mechanistic investigations suggest that the single-electron oxidation of CD₃SSO₃Na by m-CPBA generates a thiyl radical, which initiates the three-component trideuteromethylthiolative difunctionalization of alkenes. Importantly, the excellent functional group tolerance, simple reaction conditions and uniform regioselectivity of the multi-component reaction make it suitable for the late-stage functionalization of complex molecules.