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

页码：144 / 152

页数：9

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