Visible light photoredox-catalyzed deoxydisulfuration of alcohols

Abstract

Herein, we present a versatile approach for the photoredox-catalyzed deoxydisulfuration of primary, secondary, and tertiary alcohols, utilizing tetrasulfides to facilitate the efficient synthesis of unsymmetrical disulfides. The reaction mechanism involves the in situ generation of alkyloxy-2-oxoacetic acid, followed by subsequent decarboxylative alkyl radical substitution onto the tetrasulfide reagent. This method boasts several noteworthy features, including mild reaction conditions, a wide range of applicable substrates, easily obtainable starting materials, and the capability of scaling up to gram quantities. These features collectively underscore the generality and practicality of this novel disulfuration approach.