Homologation of aryl ketones to long-chain ketones and aldehydes via C–C bond cleavage

Abstract

Summary: Transition metal-catalyzed C–C bond cleavage is a powerful tool for the reconstruction of a molecular skeleton. We report herein the multi-carbon homologation of aryl ketones to long-chain ketones and aldehydes via ligand-promoted Ar−C(O) bond cleavage and subsequent cross coupling with alkenols. Various (hetero)aryl ketones are compatible in the reaction, affording the corresponding products wtih good to excellent yields with high regioselectivity. Further applications in the late-stage diversification of biologically important molecules demonstrate the synthetic utility of this protocol. Mechanistic studies indicate that the ligand plays an important role in both C–C bond cleavage and the asymmetric migration-insertion process.

Keywords

• Chemistry
• Organic chemistry
• Organic synthesis