Cu(II)-mediated oxidative dimerization of 2-phenylpyridine derivatives

被引：59

作者：

Chen, Xiao ^{[2
]}

Dobereiner, Graham ^{[2
]}

Hao, Xue-Shi ^{[2
]}

Giri, Ramesh ^{[1
]}

Maugel, Nathan ^{[2
]}

Yu, Jin-Quan ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

[2] Brandeis Univ, Dept Chem, Waltham, MA 02454 USA

来源：

TETRAHEDRON | 2009年 / 65卷 / 16期

基金：

美国国家科学基金会;

关键词：

Biaryl compounds; 2-Phenylpyridine; Palladium; Dimerization; C-H bond activation; Ullmann coupling; C-H FUNCTIONALIZATION; ELECTRON-WITHDRAWING SUBSTITUENTS; INTRAMOLECULAR RING-CLOSURE; COPPER-CATALYZED ARYLATION; ARYL BOND FORMATION; AROMATIC-COMPOUNDS; COUPLING REACTION; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; CARBONYL-COMPOUNDS;

D O I：

10.1016/j.tet.2008.10.053

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Cu(II)/I-2-mecliated C-H bond activation is described. A variety of 2-phenylpyridine derivatives are oxidatively dimerized at the ortho-position of the phenyl ring in which a net loss of two hydrogen atoms results ill [lie formation of a biaryl compound via a double C-H activation/C-C bond-forming process. Moderate functional group tolerance was observed on both the aryl and the pyridyl rings. A single electron transfer (SET) or electrophilic metalation process for iodination followed by Ullmann Coupling Of the intermediate iodinated product is proposed as the operating mechanism for the dimerization process. (C) 2008 Published by Ekevier Ltd.

引用

页码：3085 / 3089

页数：5

共 112 条

[1] Arene C-H bond activation and arene oxidative coupling by cationic palladium(II) complexes [J].