Direct Arylation of Arene C−H Bonds by Cooperative Action of NHCarbene−Ruthenium(II) Catalyst and Carbonate via Proton Abstraction Mechanism
Journal of the American Chemical Society2008Vol. 130(4), pp. 1156–1157
Citations Over TimeTop 1% of 2008 papers
İsmaıl Özdemır, Serpıl Demır, Bekır Çetınkaya, Christophe Gourlaouen, Feliu Maseras, Christian Bruneau, Pierre H. Dixneuf
Abstract
Direct functionalization of sp2 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 favored via a 13.7 kcal·mol-1 exothermic process affording an orthometalated intermediate with a 2.009 Å Ru−C bond.
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