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Hydrodecarboxylation of Carboxylic and Malonic Acid Derivatives via Organic Photoredox Catalysis: Substrate Scope and Mechanistic Insight

Jeremy D. Griffin, Mary A. Zeller and David A. Nicewicz*

*Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, United States, Email: nicewiczunc.edu

J. D. Griffin, M. A. Zeller, D. A. Nicewicz, J. Am. Chem. Soc., 2015, 137, 11340-11348.

DOI: 10.1021/jacs.5b07770 (free Supporting Information)


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Abstract

A Fukuzumi acridinium photooxidant with phenyldisulfide as a redox-active cocatalyst enable a direct, catalytic hydrodecarboxylation of primary, secondary, and tertiary carboxylic acids as well as a double decarboxylation of malonic acid derivatives. Substoichiometric quantities of Hünig’s base are used to reveal the carboxylate. Use of trifluoroethanol as a solvent allowed for significant improvements in substrate compatibilities.

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Key Words

dexarboxylation


ID: J48-Y2015