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Direct catalytic anti-Markovnikov addition of carboxylic acids to alkenes.

ABSTRACT: 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.

SUBMITTER: Perkowski AJ

PROVIDER: S-EPMC3757928 | biostudies-literature | 2013 Jul

REPOSITORIES: biostudies-literature

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Direct catalytic anti-Markovnikov addition of carboxylic acids to alkenes.

Perkowski Andrew J AJ Nicewicz David A DA

Journal of the American Chemical Society 20130703 28

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 mechanis ...[more]

PMID: 23808532

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