Research ArticleORGANIC CHEMISTRY

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

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Science Advances  29 Mar 2019:
Vol. 5, no. 3, eaav9839
DOI: 10.1126/sciadv.aav9839

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.

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