Bicyclic (alkyl)(amino)carbene (BICAAC) as a metal-free catalyst for reduction of nitriles to amines

Bicyclic (alkyl)(amino)carbene (BICAAC) is introduced as a metal-free catalyst for the reduction of various nitriles to the corresponding amine hydrochloride salts in the presence of pinacolborane. Mechanistic investigations combining experiments and DFT calculations suggest a B-H addition to the carbene center, which acts as a carrier of the hydride source. BICAAC is reported as a metal-free catalyst for the reduction of various nitriles to primary amines in the presence of pinacolborane. The B-H addition product of BICAAC plays a key catalytic role in this transformation.