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

被引：92

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

页码：14181 / 14186

页数：6

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