Tandem Catalysis: Transforming Alcohols to Alkenes by Oxidative Dehydroxymethylation

作者：Xuesong Wu, Faben A. Cruz, Alexander Lu, Vy M. Dong · 发表于：Journal of the American Chemical Society · 年份：2018 · DOI：10.1021/jacs.8b06069 · 被引用次数：56 · 研究领域：Asymmetric Hydrogenation and Catalysis、Catalytic C–H Functionalization Methods、Catalytic Cross-Coupling Reactions

We report a Rh-catalyst for accessing olefins from primary alcohols by a C-C bond cleavage that results in dehomologation. This functional group interconversion proceeds by an oxidation-dehydroformylation enabled by N, N-dimethylacrylamide as a sacrificial acceptor of hydrogen gas. Alcohols with diverse functionality and structure undergo oxidative dehydroxymethylation to access the corresponding olefins. Our catalyst protocol enables a two-step semisynthesis of (+)-yohimbenone and dehomologation of feedstock olefins.