Journal of the American Chemical Society p. 5623 - 5633 (2016)
Update date:2022-08-04
Topics: Regioselectivity Catalyst Ligand Nucleophile Chromatography Kinetics Mechanism Conjugate addition Dehydrogenation Scope Stereoselectivity Substrate Spectroscopic Analysis Oxidation state Reaction yield Thermodynamics Cu-catalyzed Saturated ketones α,β-Unsaturated carbonyl
Jie, Xiaoming
Shang, Yaping
Zhang, Xiaofeng
Su, Weiping
The first copper-catalyzed direct β-functionalization of saturated ketones is reported. This protocol enables diverse ketones to couple with a wide range of nitrogen, oxygen and carbon nucleophiles in generally good yields under operationally simple conditions. The detailed mechanistic studies including kinetic studies, KIE measurements, identification of reaction intermediates, EPR and UV-visible experiments were conducted, which reveal that this reaction proceeds via a novel radical-based dehydrogenation to enone and subsequent conjugate addition sequence.
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