Deoxycyanation of Alkyl Alcohols Using Photoredox Catalysis.

Cyano groups represent an important class of functional motifs in medicinal chemistry given their synthetic versatility and capacity to engage in essential interactions with biological targets. However, the synthesis of sterically hindered alkyl nitriles remains challenging, and, furthermore, traditional methods often rely on toxic cyanide sources. Herein, we report a photoredox-catalyzed, metal-free deoxycyanation of alkyl alcohols that allows rapid access to a wide array of 1°, 2°, and 3° cyanides using the easily handled, low-toxicity, tosyl cyanide reagent.