DOI: 10.1021/acs.joc.6c01369 ISSN: 0022-3263

Photocatalytic Dual Carbon–Carbon Bond Cleavage Cross-Coupling Reaction between Vicinal Dicarbonyl Compounds and Carboxylic Acids

Fupan Ding, Chenyuan Qu, Xiaodong Tang, Chun Zhang

Abstract

Carbon–carbon bond cleavage reactions enable the efficient recombination of two organic molecules to generate new complex organic compounds. This study developed a novel photocatalytic dual carbon–carbon bond cleavage cross-coupling reaction between vicinal dicarbonyl compounds and carboxylic acids. The reaction proceeds under mild conditions and can be used for the synthesis of target products containing sensitive chemical bonds and various heterocyclic skeletons. Through a series of control experiments, including fluorescence quenching experiments, light on/off experiments, and free radical trapping experiments, this study proposed that the reaction undergoes a free radical cross-coupling pathway involving dual carbon–carbon bond cleavage.

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