Construction of C(CO)-C(CO) Bond via NHC-Catalyzed Radical Cross-Coupling Reaction

A C(sp2)-C(sp2) bond can be constructed via a photoredox/N-heterocyclic carbene (NHC)-cocatalyzed radical cross-coupling reaction, which provides a complementary strategy to classic electron pair processes. The present protocol represents the first example of an NHC-catalyzed two-component radical cross-coupling reaction involving C(sp2)-centered radical species. The decarboxylative acylation of oxamic acid with acyl fluoride was conducted under mild conditions and allowed the preparation of a variety of useful alpha-keto amides, including sterically congested ones.

Automated summary

A C(sp2)-C(sp2) bond was formed through a photoredox/N-heterocyclic carbene (NHC)-catalyzed radical cross-coupling reaction, presenting an alternative approach to traditional electron pair processes. This method demonstrated the first example of an NHC-catalyzed two-component radical cross-coupling reaction involving C(sp2)-centered radical species. The decarboxylative acylation of oxamic acid with acyl fluoride proceeded under mild conditions, enabling the synthesis of various useful alpha-keto amides, including sterically congested compounds.