Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 143, Issue 48, Pages 20042-20048Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.1c09587
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Funding
- NIGMS [2R01GM109054]
- International Talent Training Project of Dalian Institute of Chemical Physics
- University of Chicago
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The dehydroacylation of ketones to olefins can be achieved under mild conditions through a unique reaction pathway involving aromatization-driven C-C cleavage and Cu-mediated oxidative elimination. The newly adopted MPHA reagent plays a key role in enabling efficient cleavage of ketone C-C bonds at room temperature. This method allows for the generation of diverse alkyl- and aryl-substituted olefins with broad functional group tolerance, showcasing strategic applications.
The dehydroacylation of ketones to olefins is realized under mild conditions, which exhibits a unique reaction pathway involving aromatization-driven C-C cleavage to remove the acyl moiety, followed by Cu-mediated oxidative elimination to form an alkene between the alpha and beta carbons. The newly adopted N'- methylpicolinohydrazonamide (MPHA) reagent is key to enable efficient cleavage of ketone C-C bonds at room temperature. Diverse alkyl- and aryl-substituted olefins, dienes, and special alkenes are generated with broad functional group tolerance. Strategic applications of this method are also demonstrated.
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