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Direct arylation of arene C-H bonds by cooperative action of

Direct arylation of arene C-H bonds by cooperative action of

Ozdemir, I; Demir, S; Cetinkaya, B; Gourlaouen, C; Maseras, F; Bruneau, C; Dixneuf, PH
URI: http://hdl.handle.net/11616/82714
Date: 2008

Abstract:

 
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.
 
C1 [Gourlaouen, Christophe; Maseras, Feliu] Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain.
 
[Gourlaouen, Christophe; Maseras, Feliu] Univ Autonoma Barcelona, Dept Quim, Bellaterra 08193, Catalonia, Spain.
 
[Ozdemir, Ismail; Demir, Serpil; Cetinkaya, Bekir] Inonu Univ, Fac Sci & Arts, Malatya, Turkey.
 
[Ozdemir, Ismail; Demir, Serpil; Cetinkaya, Bekir] Univ Ege, Fac Sci, Izmir, Turkey.
 
[Bruneau, Christian; Dixneuf, Pierre H.] Univ Rennes 1, Inst Sci Chim, F-35042 Rennes, France.
 

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