RhIII-Catalyzed C-H Activation: A Versatile Route towards Various Polycyclic Pyridinium Salts

被引：91
|
作者：
Luo, Ching-Zong [1 ]
Gandeepan, Parthasarathy [1 ]
Jayakumar, Jayachandran [1 ]
Parthasarathy, Kanniyappan [1 ]
Chang, Yu-Wei [1 ]
Cheng, Chien-Hong [1 ]
机构：
[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2013年 / 19卷 / 42期
关键词：
alkynes; CH activation; fluorescence; pyridinium salts; rhodium; ONE-POT SYNTHESIS; LIGHT-EMITTING-DIODES; BOND ACTIVATION; ISOQUINOLINIUM SALTS; INTERNAL ALKYNES; RHODIUM(III)-CATALYZED SYNTHESIS; CINNOLINIUM SALTS; ARYL KETONES; COMPLEXES; DERIVATIVES;
D O I：
10.1002/chem.201302290
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An efficient and convenient method for the synthesis of highly substituted polycyclic pyridinium salts from the reaction of various 2-aryl-pyridines and 2-aryl-sp(2)-nitrogen-atom-containing heterocycles with alkynes through rhodium(III)-catalyzed CH activation and annulation under an O-2 atmosphere is described. A possible mechanism that involves the chelation-assisted CH activation of the 2-aryl-pyridine substrate, insertion of the alkyne, and reductive elimination is proposed. This mechanism was supported by the isolation of a five-membered rhodacycle (I). In addition, kinetic isotope studies were performed to understand the intimate reaction mechanism.
引用
收藏
页码：14181 / 14186
页数：6
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