Direct Arylation of Arene C-H Bonds by Cooperative Action of NHCarbene-Ruthenium(II) Catalyst and Carbonate via Proton Abstraction Mechanism

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• 作者：Ismail &Ouml ; zdemir ; Serpil Demir ; Bekir Ç ; etinkaya ; Christophe Gourlaouen ; Feliu Maseras ; Christian Bruneau ; Pierre H. Dixneuf
• 刊名：Journal of the American Chemical Society
• 出版年：2008
• 出版时间：January 30, 2008
• 年：2008
• 卷：130
• 期：4
• 页码：1156 - 1157
• 全文大小：64K
• 年卷期：v.130,no.4(January 30, 2008)
• ISSN：1520-5126

文摘

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.