A general palladium-catalyzed animation of aryl halides with ammonia

Thomas Schulz, Christian Torborg, Stephan Enthaler, Benjamin Schäffner, Andreas Dumrath, Anke Spannenberg, Helfried Neumann, Armin Börner, Matthias Beller

Research output: Contribution to journalArticlepeer-review

154 Scopus citations

Abstract

A study was conducted to demonstrate palladium(Pd)-catalyzed amination of aryl halides with ammonia. The active catalyst was formed in situ from Pd(OAc)2, along with air- and moisture stable phosphines as pre-catalysts. It was found that the productivity of the catalyst system was similar to that of competitive Pd and phosphine systems. It was demonstrated that the novel electron-rich sterically demanding phosphine ligand was unable to be displaced from the palladium by ammonia to a significant extent, which prevented the deactivation of the catalyst by the ligand. It was also demonstrated that the Pd-catalyzed animation worked at ambient pressure. It was observed that the optimized system showed an excellent substrate scope including deactivated, electron-neutral, and activated halides, o-, m- p-substituted substrates, aryl chlorides, and heterocycles.

Original languageEnglish
Pages (from-to)4528-4533
Number of pages6
JournalChemistry - A European Journal
Volume15
Issue number18
DOIs
StatePublished - 27 Apr 2009
Externally publishedYes

Keywords

  • Anilines
  • Animation
  • Homogeneous catalysis
  • Palladium
  • Phosphanes

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