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

ÖZDEMİR İ., DEMIR S., CETINKAYA B., Gourlaouen C., MASERAS F., BRUNEAU C., ...Daha Fazla

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, cilt.130, sa.4, ss.1156-1158, 2008 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 130 Sayı: 4
  • Basım Tarihi: 2008
  • Doi Numarası: 10.1021/ja710276x
  • Dergi Adı: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Current Chemical Reactions (CCR)
  • Sayfa Sayıları: ss.1156-1158
  • İnönü Üniversitesi Adresli: Evet

Özet

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.