Olefination via Cu-Mediated Dehydroacylation of Unstrained Ketones
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.
Dong, Guangbin,Xu, Yan,Zhou, Xukai
supporting information
p. 20042 - 20048
(2021/12/03)
Pinacolboratamethyl-enetriphenylphosphonium iodide, a new methylene transfer reagent
The title compound is easily prepared and reacts with various aldehydes and ketone. The reagent is compatible with free hydroxy groups. Yields with various aldehydes and ketones are in 50- > 99% range. Both aliphatic, aromatic and unsaturated carbonyls react.
Al-Aziz Quntar, Abed,Srebnik, Morris
p. 2575 - 2579
(2007/10/03)
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