Hydrothiolation of terminal alkynes with diaryl disulfides and diphenyl diselenide: selective synthesis of ( Z)-1-alkenyl sulfides and selenides

Abstract

A simple, stereoselective and efficient method for the hydrothiolation of terminal alkynes with diaryl disulfides and diphenyl diselenide has been developed. In the presence of CuI, rongalite, and Cs 2CO 3, a variety of disulfides underwent the reaction of terminal alkynes stereoselectively to afford the corresponding ( Z)-1-alkenyl sulfides in moderate to excellent yields. It is noteworthy that hydroselenations of 1,2-diphenyldiselane with alkynes are also conducted smoothly to afford ( Z)-1-alkenyl selenides in good yields under the standard conditions.