Nickel-Catalyzed Selective Synthesis of α-Alkylated Ketones via Dehydrogenative Cross-Coupling of Primary and Secondary Alcohols

Herein, we describe an isolable, air-stable, homogeneous, nickel catalyst that performs dehydrogenative cross-coupling reaction between secondary and primary alcohols to result alpha-alkylated ketone products selectively. The sequence of steps involve in this one-pot reaction is dehydrogenation of both alcohols, condensation between the ketone and the aldehyde, and hydrogenation of the in situ-generated alpha,beta-unsaturated ketone. Preliminary mechanistic investigation hints a radical mechanism following borrowing hydrogen reaction.

Automated summary

The study describes an isolable, air-stable homogeneous nickel catalyst for dehydrogenative cross-coupling reaction between secondary and primary alcohols to selectively produce alpha-alkylated ketone products in a one-pot reaction. Preliminary mechanistic investigation suggests a radical mechanism following borrowing hydrogen reaction.