Direct β-Alkylation of Ketones and Aldehydes via Pd-Catalyzed Redox Cascade

J Am Chem Soc. 2018 May 16;140(19):6057-6061. doi: 10.1021/jacs.8b03530. Epub 2018 May 2.

Abstract

We report a direct β-alkylation of ketones and aldehydes with simple alkyl bromides through a Pd-catalyzed redox-cascade strategy. The use of a Cu cocatalyst is important for improved efficiency. The reaction is redox-neutral, without the need for strong acids or bases. Both cyclic and acyclic ketones, as well as α-branched aldehydes, are suitable substrates for coupling with secondary and tertiary alkyl bromides. Concise formal synthesis of Zanapezil is achieved using this β-alkylation method.

Publication types

  • Research Support, Non-U.S. Gov't