Nickel-Catalyzed Direct Substitution of Allylic Alcohols with Nitriles: A General Tool for the Construction of Acyclic C2-Tertiary or Quaternary Benzyl Nitriles

A nickel-catalyzed direct reaction of allylic alcohols with benzyl nitrile derivatives has been developed. The method provides an efficient route for the synthesis of nitriles bearing an alpha-tertiary or quaternary carbon center in good to excellent yields with high regioselectivity, wide substrate scope, and functional group compatibility. BSA was identified as the effective additive for facilitating the coupling process mainly for alkyl allylic alcohols.

Automated summary

A nickel-catalyzed direct reaction between allylic alcohols and benzyl nitrile derivatives has been developed. The method exhibits high regioselectivity, wide substrate scope, and functional group compatibility, resulting in good to excellent yields of nitriles bearing an alpha-tertiary or quaternary carbon center. BSA is identified as the effective additive for facilitating the coupling process mainly for alkyl allylic alcohols.