Potassium thiocyanate as source of cyanide for the oxidative α-cyanation of tertiary amines

J Org Chem. 2015 Mar 6;80(5):2848-54. doi: 10.1021/jo502846c. Epub 2015 Feb 11.

Abstract

Oxidation at the sulfur of the safe-to-handle potassium thiocyanate releases cyanide units that are trapped in the presence of co-oxidized tertiary amines to form α-amino nitriles. These cyanations work in aqueous solutions and do not require a catalyst, nor do they form toxic byproducts.