Rhodium-catalyzed amination of aromatic olefins [1]

Annegret Tillack, Harald Trauthwein, Christian G. Hartung, Martin Eichberger, Stephan Pitter, Achim Jansen, Matthias Beller

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

The oxidative amination of styrene with secondary amines in the presence of cationic rhodium catalysts yields regiospecifically the corresponding anti-Markovnikov enamines. Styrene as the hydrogen acceptor gave concomitantly ethylbenzene. In the presence of 1,5-cyclooctadiene (cod) preferential reduction to cyclooctene takes place. The addition of cod reduces the rate of the reaction, but also the amount of ethylbenzene produced. Here, for the first time the ratio of enamine: ethylbenzene is > 1, which is favourable in case of more expensive styrene derivatives. A screening of various ligands for oxidative amination reveals that hemilabile 2-(ω-phosphino-n-alkyl)-pyridines are superior ligands for this reaction compared to simple alkyl and aryl phosphines.

Original languageEnglish
Pages (from-to)1327-1334
Number of pages8
JournalMonatshefte für Chemie
Volume131
Issue number12
DOIs
StatePublished - 2000
Externally publishedYes

Keywords

  • Amination
  • Enamines
  • Homogeneous catalysis
  • Rhodium
  • Transition metal

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