A Reversible, Transfer Hydrocyanation Manifold

Abstract

The hydrocyanation of alkenes is a key transformation in industrial chemistry, including the production of adiponitrile. However, these industrial processes rely on the use of HCN, a notoriously toxic and volatile reagent, and thus hydrocyanation is rarely considered in routine laboratory synthesis. Our group exploited the reversible nature of C–CN oxidative addition under the effect of nickel and Lewis acid co-catalysis to realize a reversible, transfer hydrocyanation.