American Chemical Society
ja4057294_si_002.pdf (1.04 MB)

Direct Catalytic Anti-Markovnikov Addition of Carboxylic Acids to Alkenes

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journal contribution
posted on 2016-02-19, 03:28 authored by Andrew J. Perkowski, David A. Nicewicz
A direct catalytic anti-Markovnikov addition of carboxylic acids to alkenes is reported. The catalyst system is comprised of the Fukuzumi acridinium photooxidant (1) 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. A deuterium-labeling experiment lends insight to the potential mechanism.