Multicomponent reactions to access S-aryl dithiocarbamates via an electron donor-acceptor complex under open-to-air conditions.

Abstract

A simple and efficient transition-metal/photocatalyst-free visible-light-driven one-pot three-component reaction between thianthrenium salts, carbon disulfide and amines under an air atmosphere for the preparation of biologically relevant S-aryl dithiocarbamates is developed. This methodology is robust and scalable, and exhibits a broad substrate scope and excellent functional group tolerance. Of note, a wide range of primary aliphatic amines bearing different groups are suitable for this strategy. The synthetic utility was further demonstrated by a two-step one-pot multi-component reaction and photo-flow decagram-scale synthesis. Preliminary mechanistic studies suggest that the association of the dithiocarbamate anion with thianthrenium salts formed an electron donor-acceptor complex, which upon excitation with visible light produced an aryl radical via single-electron transfer.