Nickel-Catalyzed Cyanation of Unactivated Alkyl Chlorides or Bromides with Zn(CN).

A nickel-catalyzed cyanation of unactivated secondary alkyl chlorides or bromides using less toxic Zn(CN) as the cyanide source has been developed. The reaction features the use of air-stable and inexpensive NiCl·6HO or Ni(acac) as the precatalysts and offers an efficient synthesis of a broad range of alkyl nitriles. Cyanation of primary alkyl chlorides or bromides was also achieved by reaction with Zn(CN) in the presence of n-BuNCl without the need of nickel catalyst.