期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 84, 期 19, 页码 12399-12407出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b01863
关键词
-
资金
- Research Grants Council of Hong Kong [HKUST16304617]
Density functional theory calculations were carried out to study the reaction mechanisms of Ag(I)- and Zn(II)-catalyzed amination of unsaturated N-acylpyrazoles with azodicarboxylates. Our theoretical investigation focused on the origin of the metal-controlled regioselectivity (gamma- versus alpha-amination). Through our calculations, it was found that the amination reactions occur via metal-dienolate intermediates, in which the Ag(I) center prefers to coordinate with the alpha-carbon or the pyrazolyl N-donor site of the dienolate ligand, while the Zn(II) center prefers to coordinate with the O-donor of the dienolate ligand. The different site preferences for coordination with dienolate between the Ag(I) and Zn(II) metal centers play the key roles in the different regioselectivity observed experimentally.
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