Intermolecular dialkylation of alkenes with two distinct C(sp³)─H bonds enabled by synergistic photoredox catalysis and iron catalysis.

ABSTRACT: The functionalization of unactivated C(sp³)─H bonds represents one of the most powerful and most atom-economical tools for the formation of new carbon-based chemical bonds in synthesis. Although cross-dehydrogenative coupling reactions of two distinct C─H bonds for the formation of carbon-carbon bonds have been well investigated, controlled functionalizations of two or more different C(sp³)─H bonds across a functional group or a molecule (e.g., an alkene or alkyne) in a single reaction remain challenging. Here, we present a three-component dialkylation of alkenes with common alkanes and 1,3-dicarbonyl compounds via synergistic photoredox catalysis and iron catalysis for the synthesis of two functionalized 1,3-dicarbonyl compounds. Mechanistic studies suggest that the photoredox catalysis serves as a promotion system to allow the dialkylation to proceed under mild conditions by reducing the oxidation and reduction potentials of the iron intermediates and the reaction partners.

SUBMITTER: Ouyang XH 

PROVIDER: S-EPMC6440757 | biostudies-literature | 2019 Mar

REPOSITORIES: biostudies-literature