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Well-Defined Four-Coordinate Iron(II) Complexes For Intramolecular Hydroamination of Primary Aliphatic Alkenylamines

Authors

  • Dr. Elise Bernoud,

    1. Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), UMR CNRS 8182, Univ Paris-Sud, Orsay, 91405 (France)
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    • These authors contributed equally to this work.

  • Dr. Pascal Oulié,

    1. Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), UMR CNRS 8182, Univ Paris-Sud, Orsay, 91405 (France)
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    • These authors contributed equally to this work.

  • Dr. Régis Guillot,

    1. Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), UMR CNRS 8182, Univ Paris-Sud, Orsay, 91405 (France)
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  • Dr. Mohamed Mellah,

    1. Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), UMR CNRS 8182, Univ Paris-Sud, Orsay, 91405 (France)
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  • Dr. Jérôme Hannedouche

    Corresponding author
    1. Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), UMR CNRS 8182, Univ Paris-Sud, Orsay, 91405 (France)
    • Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), UMR CNRS 8182, Univ Paris-Sud, Orsay, 91405 (France)===

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  • We thank ANR JCJC DHAMFER, Univ Paris Sud and CNRS for financial support.

Abstract

Despite the growing interest in iron catalysis and hydroamination reactions, iron-catalyzed hydroamination of unprotected primary aliphatic amines and unactivated alkenes has not been reported to date. Herein, a novel well-defined four-coordinate β-diketiminatoiron(II) alkyl complex is shown to be an excellent precatalyst for the highly selective cyclohydroamination of primary aliphatic alkenylamines at mild temperatures (70–90 °C). Both empirical kinetic analyses and the reactivity of an isolated iron(II) amidoalkene dimer, [LFe(NHCH2CPh2CH2CH[DOUBLE BOND]CH2)]2 favor a stepwise σ-insertive mechanism that entails migratory insertion of the pendant alkene into an iron–amido bond associated with a rate-determining aminolysis step.

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