期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 141, 期 37, 页码 14889-14897出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b07932
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资金
- University of Chicago
A copper-catalyzed desaturation method that is suitable for converting lactones, lactams, and cyclic ketones to their alpha,beta-unsaturated counterparts is reported. The reaction does not require strong base/acid or sulfur/selenium reagents and can be carried out through a simple one-step operation. The protocol uses inexpensive catalysts and reagents and exhibits excellent scalability and functional group tolerance. Notably, tert-butyl alcohol is the only stoichiometric byproduct produced, and overoxidation is not observed. The reaction mechanism has been investigated through control experiments, deuterium labeling, radical clock, electron paramagnetic resonance, high-resolution mass spectrometry, and kinetic studies. The data obtained are consistent with a reaction pathway involving reversible alpha-deprotonation by a Cu(II)-(OBu)-Bu-t species followed by further oxidation of the resulting Cu enolate.
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