Nickel-Catalyzed Cyanation of Unactivated Alkyl Chlorides or Bromides with Zn(CN)2

A nickel-catalyzed cyanation of unactivated secondary alkyl chlorides or bromides using less toxic Zn(CN)(2) as the cyanide source has been developed. The reaction features the use of air-stable and inexpensive NiCl2 center dot 6H(2)O or Ni(acac)(2) 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)(2) in the presence of n-Bu4NCl without the need of nickel catalyst.