Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 2, Pages 735-740Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b11351
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Funding
- Shenzhen municipality [JCYJ20160226105602871]
- National Natural Science Foundation of China [21372013]
- Guangdong Natural Science Foundation [2014A030312004]
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Direct aerobic alpha,beta-dehydrogenation of gamma,delta-unsaturated amides and acids using a simple iridium/copper relay catalysis system is described. We developed a new strategy that overcomes the challenging issue associated with the low alpha-acidity of amides and acids. Instead of alpha-C-H metalation, this reaction proceeds by beta-C-H activation, which results in enhanced alpha-acidity. Conjugated dienamides and dienoic acids were synthesized in excellent yield with this reaction, which uses a simple reaction protocol. Mechanistic experiments suggest a catalyst resting state mechanism in which both alpha-C-H and beta-C-H cleavage is accelerated.
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