Direct synthesis of 1,3-dithiolanes from terminal alkynes via visible light photoredox catalysis

Abstract

A visible light-mediated, metal-free, regioselective dihydrothionation of terminal aromatic as well as heteroaromatic alkynes has been achieved using Eosin Y as a photoredox catalyst at room temperature. The protocol gives direct access to different 1,3-dithiolanes under neutral and mild reaction conditions without the use of any base or additives. The electron-donating, electron-withdrawing and electron-deactivating groups tolerated the photocatalytic reaction conditions. The control experiments, cyclic voltammetry, and Stern–Volmer experiment were carried out to gain an insight into the mechanistic pathway. The protocol proved to be scalable at the gram level and also for practicality the deprotection of 1,3-dithiolanes has been demonstrated. The method uses clean energy under sustainable conditions.