Reaction of Fischer Alkynyl Carbene Complexes with Fluorenone Imines: Mechanistic Studies

  1. Rivado-Casas, L. 1
  2. Campos, P.J. 1
  3. Sampedro, D. 1
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

Revue:
Organometallics

ISSN: 0276-7333

Année de publication: 2010

Volumen: 29

Número: 14

Pages: 3117-3124

Type: Article

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DOI: 10.1021/OM100219H SCOPUS: 2-s2.0-77955890126 WoS: WOS:000279928400007 GOOGLE SCHOLAR

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Résumé

The reaction of Fischer carbene complexes with imines to yield fluorenylidene-pyrroline molecular switches has been explored. A combined experimental and theoretical study was carried out to understand the reaction mechanism. Experimental and theoretical data are in good agreement, which allows delimiting the reaction outcome. Nucleophilic attack of the imine to alkyne is the first step in the reaction path and the one with a higher energy barrier. The most stable intermediate was isolated from the reaction mixture, thus supporting the proposed mechanism. The different reaction outcome when using fluorenone or benzophenone imines was investigated with diverse imine moieties. The effect of substitution in both imine and carbene complexes was also explored in order to increase the reaction's scope. © 2010 American Chemical Society.