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
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
收藏
页码:586 / 591
页数:6
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