Development of an Operationally Simple, Scalable, and HCN-Free Transfer Hydrocyanation Protocol Using an Air-Stable Nickel Precatalyst

Hydrocyanation reactions enable access to synthetically valuable nitriles from readily available alkene precursors. However, hydrocyanation using hydrogen cyanide (HCN) or similarly toxic reagents on laboratory scale can be particularly challenging due their hazardous nature. In addition, such processes typically require air- and temperature-sensitive Ni(0) precatalysts, further reducing the operational simplicity of this transformation. Herein, we report a HCN-free transfer alkenes alkynes that employs commercially aliphatic as sacrificial HCN donors in combination with catalytic amount air-stable inexpensive NiCl2 precatalyst cocatalytic Lewis acid. The scalability robustness process were demonstrated by ?-methylstyrene 100 mmol (11.4 g product obtained) 1 mol % Ni catalyst. feasibility dehydrocyanation protocol Ni(II) norbornadiene acceptor was showcased selective conversion an nitrile into corresponding alkene.