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Synthesis
DOI: 10.1055/a-2722-7001
Paper

Asymmetric Kumada-Tamao-Corriu Cross-Coupling Catalyzed by Chiral Pd(NHC) Complexes

Authors

  • Paul R. Guerin

    1   iSm2, Aix Marseille Univ, CNRS, Centrale Med, Marseille, France

  • Yajie Chou

    1   iSm2, Aix Marseille Univ, CNRS, Centrale Med, Marseille, France

  • Sophie Ronzière

    1   iSm2, Aix Marseille Univ, CNRS, Centrale Med, Marseille, France

  • Muriel Serradeil-Albalat

    1   iSm2, Aix Marseille Univ, CNRS, Centrale Med, Marseille, France
    2   FSCM – UAR 1739, Chiropole, Aix Marseille Univ, CNRS, Centrale Med, Marseille, France

  • Marion Jean

    1   iSm2, Aix Marseille Univ, CNRS, Centrale Med, Marseille, France
    2   FSCM – UAR 1739, Chiropole, Aix Marseille Univ, CNRS, Centrale Med, Marseille, France

  • Nicolas Vanthuyne

    1   iSm2, Aix Marseille Univ, CNRS, Centrale Med, Marseille, France
    2   FSCM – UAR 1739, Chiropole, Aix Marseille Univ, CNRS, Centrale Med, Marseille, France

  • Damien Hérault

    1   iSm2, Aix Marseille Univ, CNRS, Centrale Med, Marseille, France

  • Hervé Clavier 

    1   iSm2, Aix Marseille Univ, CNRS, Centrale Med, Marseille, France
    3   ICR, Aix Marseille Univ, CNRS, Marseille, France

Gefördert durch: Région Provence-Alpes-Côte d’Azur project 2022_03860 Chirasalt
Gefördert durch: China Scholarship Council
Gefördert durch: Agence Nationale de la Recherche 2022_03860,ANR-20-CE07-0030
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The Kumada-Tamao-Corriu cross-coupling affording axially chiral biaryl compounds has been investigated with various chiral Pd(NHC) complexes (NHC = N-heterocyclic carbene). While the nature of the aryl halide partner did not have an influence on the enantioselectivity, the enantioenrichment of coupling products was found to be highly dependent on the structure of the arylmagnesium halide but also on the chiral Pd(NHC) complex used. Thus, up to 63% ee was achieved using an atropisomeric Pd(NHC) complex. These data, along with role reversal experiments of cross-coupling partners, suggest the reductive elimination step to be likely rate- and enantio-determining.



Publikationsverlauf

Eingereicht: 03. Juni 2025

Angenommen nach Revision: 13. Oktober 2025

Accepted Manuscript online:
13. Oktober 2025

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