Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality

Angew Chem Int Ed Engl. 2009;48(28):5094-115. doi: 10.1002/anie.200806273.


In the past decade, palladium-catalyzed C-H activation/C-C bond-forming reactions have emerged as promising new catalytic transformations; however, development in this field is still at an early stage compared to the state of the art in cross-coupling reactions using aryl and alkyl halides. This Review begins with a brief introduction of four extensively investigated modes of catalysis for forming C-C bonds from C-H bonds: Pd(II)/Pd(0), Pd(II)/Pd(IV), Pd(0)/Pd(II)/Pd(IV), and Pd(0)/Pd(II) catalysis. A more detailed discussion is then directed towards the recent development of palladium(II)-catalyzed coupling of C-H bonds with organometallic reagents through a Pd(II)/Pd(0) catalytic cycle. Despite the progress made to date, improving the versatility and practicality of this new reaction remains a tremendous challenge.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Review

MeSH terms

  • Alkenes / chemistry
  • Catalysis
  • Crystallography, X-Ray
  • Molecular Conformation
  • Organometallic Compounds / chemistry
  • Palladium / chemistry*
  • Stereoisomerism


  • Alkenes
  • Organometallic Compounds
  • Palladium