Anti-Markonikov reactions, 6. Rhodium-catalyzed amination of vinylpyridines: Hydroamination versus oxidative amination

Matthias Beller, Harald Trauthwein, Martin Eichberger, Claudia Breindl, Thomas E. Müller

Research output: Contribution to journalArticlepeer-review

94 Scopus citations

Abstract

Cationic rhodium complexes catalyze the amination of 2- and 4- vinylpyridine with secondary amines. Depending on the substrate and the reaction conditions either oxidative amination to yield the corresponding enamines 1a-8a or hydroamination to give 2-aminoethylpyridines 1b-8b occurs. In all cases products with anti-Markovnikov regioselectivity are obtained. For mechanistic studies novel cationic complexes of rhodium(I)-containing cyclooctadiene and vinylpyridine 12 as well as complexes containing cyclooctadiene, vinylpyridine, and morpholine 13 were prepared and characterized by NMR spectroscopy and X-ray diffraction analysis.

Original languageEnglish
Pages (from-to)1121-1132
Number of pages12
JournalEuropean Journal of Inorganic Chemistry
Issue number7
DOIs
StatePublished - 1999
Externally publishedYes

Keywords

  • Aminations
  • Coordination chemistry
  • Hydroaminations
  • Oxidative aminations
  • Rhodium
  • Vinylpyridines

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