Mechanistic DFT Study on Rhodium(III)-Catalyzed Double C-H Activation for Oxidative Annulations of 2-Substituted Imidazoles and Alkynes

被引：11

作者：

Xie, Peipei ^{[1
]}

Jia, Mengmeng ^{[1
]}

Xu, Xiao-Hua ^{[2
]}

Chen, Fan ^{[1
]}

Xia, Yuanzhi ^{[1
]}

机构：

[1] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China

[2] Wenzhou Univ, Coll Math Phys & Elect Informat Engn, Wenzhou 325035, Peoples R China

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 7卷 / 03期

基金：

中国国家自然科学基金;

关键词：

C-H activation; density functional calculations; directing-group-free reactions; reaction mechanisms; rhodium(III) catalysis; N BOND; ACTIVATION/CYCLOADDITION REACTIONS; REGIOSELECTIVE SYNTHESIS; CATALYZED ANNULATION; DENSITY FUNCTIONALS; CARBOXYLIC-ACIDS; DIRECTING GROUPS; METAL; ARENES; SELECTIVITY;

D O I：

10.1002/ajoc.201700625

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mechanistic understanding of the rhodium(III)catalyzed double C-H activation for oxidative annulations of 2-substituted imidazoles and alkynes was achieved by density functional theory calculations. It is disclosed that the rhodium(III)-acetate-triggered C-H bond cleavage occurs without a directing group, and the C5-H cleavage has the lowest activation barrier among all possible C-H activation processes. The experimental observations in reactions of different imidazole derivatives were explained well by the theoretical results.

引用

页码：586 / 591

页数：6

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