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Versatile Palladium-Catalyzed Approach to Acyl Fluorides and Carbonylations by Combining Visible Light- and Ligand-Driven Operations

Yi Liu, Cuihan Zhou, Meijing Jiang and Bruce A. Arndtsen*

*Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 0B8, Canada, Email: bruce.arndtsenmcgill.ca

Y. Liu, C. Zhou, M. Jiang, B. A. Arndtsen, J. Am. Chem. Soc., 2022, 144, 9413-9420.

DOI: 10.1021/jacs.2c01951


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Abstract

A general palladium-catalyzed carbonylative synthesis of acyl fluorides from aryl, heteroaryl, alkyl, and functionalized organic halides proceeds via a synergistic combination of visible light photoexcitation of Pd(0) to induce oxidative addition with a ligand-favored reductive elimination. Subsequent nucleophilic reactions provide highly functionalized carbonyl-containing products.

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Key Words

carboxylation (arenes, alkanes), acyl fluorides, multicomponent reactions, photochemistry


ID: J48-Y2022