Improved palladium-catalyzed sonogashira coupling reactions of aryl chlorides

Christian Torborg, Jun Huang, Thomas Schulz, Benjamin Schäffner, Alexander Zapf, Anke Spannenberg, Armin Borner, Matthias Beller

Research output: Contribution to journalArticlepeer-review

111 Scopus citations

Abstract

The improved palladium-catalyzed Sonogashira coupling reactions of aryl chlorides without the necessity to add copper salts were analyzed for the development of palladacycles, adamantylphosphines, carhene ligands, and 2-phosphino-N-arylin-doles and -pyrroles. The synthesis of 2-phosphino-N- arylimidazoles and their application in cross-coupling reactions of aryl chlorides and bromides was also analyzed. The experiment showed good to excellent coupling results of a variety of aryl and heteroaryl chlorides including challenging substrates have been obtained in the presence of [N-(2,6- diisopropylphenyl)-2-imidazolyl-di-tert-butylphosphine Li at low catalyst loading. The result also showed that the importance of the novel procedure as a cost effective and benign with respect to solvent, base, and avoiding the addition of copper salts.

Original languageEnglish
Pages (from-to)1329-1336
Number of pages8
JournalChemistry - A European Journal
Volume15
Issue number6
DOIs
StatePublished - 26 Jan 2009
Externally publishedYes

Keywords

  • Aryl chlorides
  • C-C coupling
  • Homogeneous catalysis
  • Palladium
  • Phosphane ligands
  • Sonogashira reaction

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