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A Unified Approach to Decarboxylative Halogenation of (Hetero)aryl Carboxylic Acids

Tiffany Q. Chen, P. Scott Pedersen, Nathan W. Dow, Remi Fayad, Cory E. Hauke, Michael C. Rosko, Evgeny O. Danilov, David C. Blakemore, Anne-Marie Dechert-Schmitt, Thomas Knauber, Felix N. Castellano and David W. C. MacMillan*

*Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, United States, Email:

T. Q. Chen, P. Scott Pedersen, N. W. Dow, R. Fayad, C. E. Hauke, M. S. Rosko, E. O. Danilov, D. C. Blakemore, A.-M. Dechert-Schmitt, T. Knauber, F. N. Castelano, D. W. C. MacMillan, J. Am. Chem. Soc., 2022, 144, 8296-8305.

DOI: 10.1021/jacs.2c02392

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A catalytic decarboxylative halogenation of (hetero)aryl carboxylic acids accommodates an exceptionally broad scope of substrates. The generated aryl radical intermediate enables divergent functionalization pathways: (1) atom transfer to access bromo- or iodo(hetero)arenes or (2) radical capture by copper and subsequent reductive elimination to generate chloro- or fluoro(hetero)arenes.

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Key Words

bromination, decarboxylation, DBDMH, photochemistry

ID: J48-Y2022