Department of Chemistry , University of Chicago , Chicago , Illinois 60637 , United States.
J Am Chem Soc. 2018 May 16;140(19):6057-6061. doi: 10.1021/jacs.8b03530. Epub 2018 May 2.
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.
我们报告了一种通过钯催化的氧化还原级联策略,实现酮和醛与简单的烷基溴化物的直接β-烷基化反应。使用铜助催化剂对于提高效率很重要。该反应是氧化还原中性的,不需要强酸或强碱。环状和非环状酮以及α-支链醛都是与仲烷基和叔烷基溴化物偶联的合适底物。使用这种β-烷基化方法实现了 Zanapezil 的简洁的全合成。