Nickel-Catalysis Enabling α-Alkylation of Ketones by Secondary Alcohols

Abstract

The α-alkylation of ketones utilizing a secondary alcohol has been accomplished by an isolable, bench-stable, inexpensive nickel catalyst affording high yields of β,β-disubstituted products. This report contributes a nickel catalyst in the pool of a few scarce examples of base metal discovered for this purpose. The substrate scope can span a wide range including aliphatic, alicyclic, and cyclic secondary alcohols. Functionalization of a cholesterol molecule is also possible following this methodology. The catalyst can interconvert between azo and hydrazo form in a reversible fashion to enable this chemical transformation.