Ag 催化 N-芳基-α-重氮酰胺合成 3-亚烷基氧吲哚的反应机理的理论研究：Lewis 酸还是 Ag-卡宾途径？
Theoretical study on the mechanism of Ag-catalyzed synthesis of 3-alkylideneoxindoles from N-aryl-α-diazoamides: a Lewis acid or Ag-carbene pathway?
机构信息
Department of Applied Chemistry, China Agricultural University, Beijing, China.
出版信息
Org Biomol Chem. 2012 Aug 21;10(31):6294-8. doi: 10.1039/c2ob25581b. Epub 2012 Jun 26.
PMID:22733091
Abstract
The mechanism of the title reaction is found to consist of three steps by DFT calculations: (1) N(2) dissociation, (2) intramolecular Ag-carbene addition, and (3) proton transfer. The N(2) dissociation is turnover determining. The product 3-alkylideneoxindole is favored in tautomerization with 3-acetyl-2-hydroxyindole.
摘要
通过 DFT 计算，发现标题反应的机理由三个步骤组成：（1）N2 解离，（2）分子内 Ag-卡宾加成，（3）质子转移。N2 解离是周转率决定的。产物 3-亚烷基-3-乙酰基-2-羟基吲哚在互变异构中有利于 3-乙酰基-2-羟基吲哚。
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