Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 135, Issue 28, Pages 10334-10337Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja4057294
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Funding
- National Institute of General Medical Sciences [R01 GM098340]
- University of North Carolina at Chapel Hill
- Packard Foundation
- Eli Lilly New Faculty Award
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A direct catalytic anti-Markovnikov addition of carboxylic acids to alkenes is reported. The catalyst system is comprised of the Fukuzumi acridinium photo-oxidant (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.
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