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Direct Catalytic Anti-Markovnikov Addition of Carboxylic Acids to Alkenes

Andrew J. Perkowski 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

A. J. Perkowski, D. A. Nicewicz, J. Am. Chem. Soc., 2013, 135, 10334-10337.

DOI: 10.1021/ja4057294


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Abstract

A direct catalytic anti-Markovnikov addition of carboxylic acids to alkenes is comprised of the Fukuzumi acridinium photooxidant and a substoichiometric quantity of a hydrogen-atom donor. Oxidizable olefins, such as styrenes, trisubstituted aliphatic alkenes, and enamides, can be employed along with a variety of carboxylic acids to afford the anti-Markovnikov addition adducts exclusively.

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ID: J48-Y2013