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

Ismail Özdemir, Serpil Demir, Bekir Çetinkaya, Christophe Gourlaouen, Feliu Maseras, Christian Bruneau, Pierre H. Dixneuf

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322 Citations (Scopus)

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 RuCl 2 (NHC) unit and generated from [RuCl 2 (arene)] 2 and two types of NHC precursors, pyrimidinium and benzimidazolium salts, in the presence of Cs 2 CO 3 . DFT calculations from RuCl 2 (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. Copyright © 2008 American Chemical Society.
Original languageEnglish
Pages (from-to)1156-1157
JournalJournal of the American Chemical Society
Volume130
Issue number4
DOIs
Publication statusPublished - 30 Jan 2008

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