posted on 2021-11-22, 17:34authored byXukai Zhou, Yan Xu, Guangbin Dong
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 α and β
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.