The mechanism of Cu-catalyzed C-N cyclization from N-phenylbenzamidine to 2-phenylbenzimidazole: A DFT study

被引：14

作者：

Ruan, Gui-Yu ^{[1
]}

Zhang, Ye ^{[1
]}

Qi, Zheng-Hang ^{[1
]}

Ai, Dong-Xia ^{[1
]}

Liu, Wei ^{[1
]}

Wang, Yong ^{[1
]}

机构：

[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Suzhou 215123, Peoples R China

来源：

COMPUTATIONAL AND THEORETICAL CHEMISTRY | 2015年 / 1054卷

关键词：

Copper catalyst; N-H activation; Density functional theory; H BOND ACTIVATION; ARYLATION; FUNCTIONALIZATION; AMINATION; SELECTIVITIES; ALKENYLATION; LIGANDS; INDOLES; ROUTE;

D O I：

10.1016/j.comptc.2014.12.008

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：

Possible mechanisms of copper-catalyzed N-H/C-H activation from N-phenylbenzamidine to 2-phenyl-benzimidazole have been investigated using density functional theory (DFT) calculations. In comparison with the C-H activation mechanism, the N-H/C-H activation with a Cu-assisted concerted metalation deprotonation (CMD) mechanism is found to be more kinetically favorable. Facile occurrence of the studied reactions is supported by the low activation energies of their respective rate-determining steps. A possible alternative mechanism involving a Cu-H agostic transition state is presented, but it is unfavored by the relatively higher activation barriers. (C) 2014 Elsevier B.V. All rights reserved.

引用

页码：16 / 21

页数：6

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