Direct arylation of arene C-H bonds by cooperative action of NHCarbene-Ruthenium(II) catalyst and carbonate via proton abstraction mechanism

被引：344

作者：

Ozdemir, Ismail ^{[3
,4
]}

Demir, Serpil ^{[3
,4
]}

Cetinkaya, Bekir ^{[3
,4
]}

Gourlaouen, Christophe ^{[1
,2
]}

Maseras, Feliu ^{[1
,2
]}

Bruneau, Christian ^{[5
]}

Dixneuf, Pierre H. ^{[5
]}

机构：

[1] Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain

[2] Univ Autonoma Barcelona, Dept Quim, Bellaterra 08193, Catalonia, Spain

[3] Inonu Univ, Fac Sci & Arts, Malatya, Turkey

[4] Univ Ege, Fac Sci, Izmir, Turkey

[5] Univ Rennes 1, Inst Sci Chim, F-35042 Rennes, France

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 04期

关键词：

D O I：

10.1021/ja710276x

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Direct functionalization of sp(2) C-H bonds via ortho diarylation of 2-pyridyl benzene with arylbromides was achieved using ruthenium(II) catalysts containing a RuCl2(NHC) unit and generated from [RuCl2(arene)](2) and two types of NHC precursors, pyrimidinium and benzimidazolium salts, in the presence of Cs2CO3. DFT calculations from RuCl2(NHC)(2-pyridylbenzene) show that a proton abstraction mechanism, on cooperative actions of both the coordinated base and the Ru(II) center, is favoured via a 13.7 kcal mol(-1) exothermic process affording an orthometalated intermediate with a 2.009 angstrom Ru-C bond.

引用

页码：1156 / +

页数：3

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