Nickel-Catalyzed Hydrocyanoalkylation of Terminal Alkynes: A Route to Tetrasubstituted ( Z )-Alkenyl Nitriles

Alkenyl nitriles represent an important structural motif in medicinal chemistry. However, efficient and general methods for the stereoselective synthesis of their tetrasubstituted ( Z )-alkenyl nitriles remain a significant challenge. Herein, we report a nickel-catalyzed reductive coupling that enables the direct hydrocyanoalkylation of terminal alkynes with readily available α-bromonitriles. This operationally simple protocol proceeds under mild conditions and exhibits a broad substrate scope, providing efficient access to a diverse array of tetrasubstituted ( Z )-alkenyl nitriles with good stereoselectivity. The utility of this method is further highlighted by its successful application to the late-stage modification of bioactive molecules.