C ̶ C Bond Formation of Benzyl Alcohols and Alkynes using Catalytic Amount of KOtBu: Unusual Regioselectivity via a Radical Mechanism

We report the C‐C bond‐forming reaction of benzyl alcohols and alkynes using a catalytic amount of KOtBu to form α‐alkylated ketones in which the C=O group is located on the side derived from the alcohol, a reaction that has not been reported yet in the peer‐reviewed literature. The reaction proceeds under thermal condition (125 oC) 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.

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