Site-specific phenylation of pyridine catalyzed by phosphido-bridged ruthenium dimer complexes: a prototype for C-H arylation of electron-deficient heteroarenes

J Am Chem Soc. 2005 Mar 23;127(11):3648-9. doi: 10.1021/ja042510p.

Abstract

Direct and selective catalytic arylation of alpha-C-H bond in pyridine with iodobenzene was achieved in up to 70% yield. Phosphido-bridged bisruthenium complexes 6a and 6b arising from Ru3(CO)12 and PPh3 were identified as active catalysts. The formation of complexes 6a and 6b was investigated, a sequence of C-H and C-P bond cleavage, cluster fragmentation, and disproportionation was established, and the intermediate ruthenium complexes lying on this pathway were isolated and fully characterized.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Benzene Derivatives / chemical synthesis*
  • Benzene Derivatives / chemistry
  • Catalysis
  • Dimerization
  • Iodobenzenes / chemistry
  • Organophosphorus Compounds / chemistry*
  • Phosphines / chemistry
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry
  • Ruthenium / chemistry*

Substances

  • Benzene Derivatives
  • Iodobenzenes
  • Organophosphorus Compounds
  • Phosphines
  • Pyridines
  • Ruthenium
  • iodobenzene