Metal-free synthesis of alkynyl alkyl selenides via three-component coupling of terminal alkynes, Se, and epoxides

Abstract

A metal-free three-component coupling reaction of alkynes, Se powder and epoxides is described for the first time. This reaction provides an efficient and straightforward route for the preparation of alkynyl alkyl selenides via a double C–Se bond formation process. Preliminary investigations revealed that elemental Se played a dual role, first serving as an oxidant with the resulting selenide anion then reacting with epoxides to form an active dialkyl diselenide intermediate.