New ligands for a general palladium-catalyzed amination of aryl and heteroaryl chlorides

Franck Rataboul, Alexander Zapf, Ralf Jackstell, Surendra Harkal, Thomas Riermeier, Axel Monsees, Uwe Dingerdissen, Matthias Beller

Research output: Contribution to journalArticlepeer-review

276 Scopus citations

Abstract

The synthesis and application of monodentate N-substituted heteroarylphosphines is described. In general, the ligands are conveniently prepared by selective metallation at the 2-position of the respective N-substituted heterocycle (pyrrole, indole) by using n-butyllithium/ tetramethylethylenediamine (TMEDA) followed by quenching with dialkyl- or diarylchlorophosphines. Of the different ligands prepared, the new dialkyl-2-(N-arylindolyl)phosphines (cataCXium® P) perform excellently in the palladium-catalyzed amination of aryl and heteroaryl chlorides. Coupling of both activated and deactivated chloroarenes proceeds under mild conditions (room temperature to 60°C). By using optimized conditions remarkable catalyst productivity (total turnover number, TON, up to 8000) and activity (turnover frequency, TOF = 14000 h-1 at 75% conversion) are observed.

Original languageEnglish
Pages (from-to)2983-2990
Number of pages8
JournalChemistry - A European Journal
Volume10
Issue number12
DOIs
StatePublished - 21 Jun 2004
Externally publishedYes

Keywords

  • Amination
  • Anilines
  • Aryl chlorides
  • Catalysis
  • Palladium
  • Phosphines

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