Intermolecular dialkylation of alkenes with two distinct C(sp<sup>3</sup>)─H bonds enabled by synergistic photoredox catalysis and iron catalysis.
basic_science · Level V
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- Record sourced from PubMed, PMID 30944866.
- Also identified by DOI 10.1126/sciadv.aav9839 and PMC identifier 6440757.
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Abstract
The functionalization of unactivated C(sp<sup>3</sup>)─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(sp<sup>3</sup>)─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.