C-C Bond Formation of Benzyl Alcohols and Alkynes Using a Catalytic Amount of KO Bu: Unusual Regioselectivity through a Radical Mechanism.

We report a C-C bond-forming reaction between benzyl alcohols and alkynes in the presence of a catalytic amount of KO Bu to form α-alkylated ketones in which the C=O group is located on the side derived from the alcohol. The reaction proceeds under thermal conditions (125 °C) and produces no waste, making the reaction highly atom efficient, environmentally benign, and sustainable. Based on our mechanistic investigations, we propose that the reaction proceeds through radical pathways.