Selectively synthesis of cyclic di- and trithiocarbonates by N-heterocyclic carbene/LiCl(Br) catalyzed addition of carbon disulfide to epoxides

Carbon disulfide is an abundant, inexpensive and readily available material. One of the main challenges in the reaction of epoxides with CS2 is to control the chemoselectivity as a variety of compounds would be formed in the reaction. A simple and convenient method toward selectively synthesis of oxathiolane and trithiocarbonate from epoxides with CS2 catalyzed by NHC/LiCI(Br) under the neat conditions has been developed. This catalytic system exhibits excellent activity and selectivity in cycloaddition reactions of carbon disulfide to terminal epoxides. (C) 2017 Elsevier Ltd. All rights reserved.