Thiol-yne reaction

[1][2] The reaction was first reported in 1949 with thioacetic acid as reagent[3][4] and rediscovered in 2009.

The radical intermediate can engage in secondary reactions such as cyclisation.

Reported catalysts for radical additions are triethylborane,[11] indium(III) bromide[12] and AIBN.

[20] Diphenyl disulfide reacts with alkynes to a 1,2-bis(phenylthio)ethylene.

[5][37] Another reported application is the synthesis of macrocycles via dithiol coupling.