Mechanisms of Csp3-H functionalization of ethyl 2-(methyl(p-tolyl)amino)acetate: A theoretical investigation

被引：12
|
作者：
Zhou, Da-Gang [1 ]
Zhou, Pan-Pan [1 ]
Jing, Huan-Wang [1 ]
机构：
[1] Lanzhou Univ, Dept Chem, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China
来源：
COMPUTATIONAL AND THEORETICAL CHEMISTRY | 2017年 / 1118卷
基金：
中国国家自然科学基金;
关键词：
Ethyl 2-(methyl(p-tolyl)amino)acetate; DFT; TRIARYLPHOSPHINE RADICAL CATIONS; FRONTIER-ELECTRON THEORY; GENERAL-METHOD; ISATINS; ACTIVATION; REACTIVITY; INDIRUBIN; OXIDATION; BONDS;
D O I：
10.1016/j.comptc.2017.09.003
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
The mechanisms for the Csp(3)-H functionalization of ethyl 2-(methyl(p-tolyl)amino)acetate have been investigated using DFT method at the M06-2X/6-31+G(d, p) level, and the SMD model was applied to simulate the solvent effect. The computational results show that the Csp3-H functionalization has four possible paths to generate intermediate radical. Then addition reaction happens between the radical and O-2 molecule. Finally, the addition product can convert into 1,5-dimethylindoline-2,3-dione via two different paths. The results could provide valuable insights into these types of interactions and related ones. (C) 2017 Elsevier B.V. All rights reserved.
引用
收藏
页码：144 / 152
页数：9
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