Tandem Catalysis: Transforming Alcohols to Alkenes by Oxidative Dehydroxymethylation.
Xuesong WuFaben A CruzAlexander LuVy M DongPublished in: Journal of the American Chemical Society (2018)
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.