Deacetylative cyanation: a cyanide-free route to thiocyanates and cyanamides

Abstract

The use of N-hydroxy-2-oxopropanimidoyl chloride as a latent cyanide transfer agent is reported. This easy-to-handle, scalable, and operationally simple agent can be installed on common nucleophiles, including thiols and secondary amines, affording synthetically useful thiocyanates and cyanamides. This method complements conventional approaches that use poisonous and volatile cyanogen halides.