Visible-light-induced carbonylative atom transfer radical addition of alkenes: straightforward preparation of branched unsaturated thioesters

Abstract

Carbonylation is a straightforward methodology for the preparation of carbonyl-containing compounds, which are one of the core classes of compounds in pharmaceutical chemistry and industrial production. Among the developed carbonylation procedures, methods for branched unsaturated compounds are much less studied compared with their linear derivatives. However, their unique chemical structure and properties make them irreplaceable in numerous fields. Herein, we report a new visible-light-induced photocatalytic carbonylative atom transfer radical addition reaction of alkenes. The reaction proceeds effectively with 100% atom efficiency and produced various thioesters in good yields. Then, the product also led to efficient synthesis of branched unsaturated thioesters by simple base-mediated desulfonylation with recyclable arylsulfinic acid eliminated. Remarkably, besides their own importance, thioesters can also be used as acyl donors to produce important compounds such as ketones, aldehydes, esters, amides, and acyl silicon reagents.

Keywords: Carbonylation; Alkene; Unsaturated thioester; Radical addition; Photochemistry.