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Selective Reduction of Esters to Aldehydes under the Catalysis of Well-Defined NHC–Iron Complexes

Authors

  • Haoquan Li,

    1. UMR 6226 CNRS—Université de Rennes 1, Institut des Sciences Chimiques de Rennes, Team Organometallics: Materials and Catalysis, Centre for Catalysis and Green Chemistry, Bat 10C, Campus de Beaulieu, 35042 Rennes Cedex (France)
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    • These authors contributed equally.

  • Dr. Luis C. Misal Castro,

    1. UMR 6226 CNRS—Université de Rennes 1, Institut des Sciences Chimiques de Rennes, Team Organometallics: Materials and Catalysis, Centre for Catalysis and Green Chemistry, Bat 10C, Campus de Beaulieu, 35042 Rennes Cedex (France)
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    • These authors contributed equally.

  • Jianxia Zheng,

    1. UMR 6226 CNRS—Université de Rennes 1, Institut des Sciences Chimiques de Rennes, Team Organometallics: Materials and Catalysis, Centre for Catalysis and Green Chemistry, Bat 10C, Campus de Beaulieu, 35042 Rennes Cedex (France)
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  • Dr. Thierry Roisnel,

    1. UMR 6226 CNRS—Université de Rennes 1, Institut des Sciences Chimiques de Rennes, Centre de Diffractométrie X, Bat 10B, Campus de Beaulieu, 35042 Rennes Cedex (France)
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  • Dr. Vincent Dorcet,

    1. UMR 6226 CNRS—Université de Rennes 1, Institut des Sciences Chimiques de Rennes, Centre de Diffractométrie X, Bat 10B, Campus de Beaulieu, 35042 Rennes Cedex (France)
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  • Dr. Jean-Baptiste Sortais,

    Corresponding author
    1. UMR 6226 CNRS—Université de Rennes 1, Institut des Sciences Chimiques de Rennes, Team Organometallics: Materials and Catalysis, Centre for Catalysis and Green Chemistry, Bat 10C, Campus de Beaulieu, 35042 Rennes Cedex (France)
    • UMR 6226 CNRS—Université de Rennes 1, Institut des Sciences Chimiques de Rennes, Team Organometallics: Materials and Catalysis, Centre for Catalysis and Green Chemistry, Bat 10C, Campus de Beaulieu, 35042 Rennes Cedex (France)
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  • Prof. Dr. Christophe Darcel

    Corresponding author
    1. UMR 6226 CNRS—Université de Rennes 1, Institut des Sciences Chimiques de Rennes, Team Organometallics: Materials and Catalysis, Centre for Catalysis and Green Chemistry, Bat 10C, Campus de Beaulieu, 35042 Rennes Cedex (France)
    • UMR 6226 CNRS—Université de Rennes 1, Institut des Sciences Chimiques de Rennes, Team Organometallics: Materials and Catalysis, Centre for Catalysis and Green Chemistry, Bat 10C, Campus de Beaulieu, 35042 Rennes Cedex (France)
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  • We are grateful to the CNRS, the University of Rennes 1, and the Ministère de l’Enseignement Supérieur et de la Recherche for support. We also thank the Ministère des Affaires Etrangères and the Fundación Gran Mariscal de Ayacucho (grant to L.C.M.C.), the Foundation Rennes 1 (grant to H.L.), and Axa Research Funds (grant to J.Z.). NHC=N-heterocyclic carbene.

Abstract

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On a direct course to the aldehyde: Hydrosilylation catalyzed by a well-defined N-heterocyclic-carbene–iron complex under UV irradiation enabled the selective reduction of esters to aldehydes (see scheme; Bn=benzyl, Mes=mesityl). The low catalyst loading and very mild reaction conditions make this chemoselective transformation a promising alternative to the reduction of esters with diisobutylaluminum hydride.

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