Reversible 1,4-Insertion of Pyridine Into a Highly Polar Metal–Carbon Bond: Effect of the Second Metal

Authors

  • Dipl.-Chem. Crispin Lichtenberg,

    1. Institut für Anorganische Chemie, RWTH Aachen University, Landoltweg 1, 52056 Aachen (Germany), Fax: (+49) 241-80-92644
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  • Dr. Thomas P. Spaniol,

    1. Institut für Anorganische Chemie, RWTH Aachen University, Landoltweg 1, 52056 Aachen (Germany), Fax: (+49) 241-80-92644
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  • Dr. Lionel Perrin,

    1. Université de Toulouse et CNRS, INSA, UPS, CNRS, UMR 5215 LPCNO, 135 avenue de Rangueil, 31077 Toulouse (France), Fax: (+33) 561-559-697
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  • Prof. Dr. Laurent Maron,

    Corresponding author
    1. Université de Toulouse et CNRS, INSA, UPS, CNRS, UMR 5215 LPCNO, 135 avenue de Rangueil, 31077 Toulouse (France), Fax: (+33) 561-559-697
    • Université de Toulouse et CNRS, INSA, UPS, CNRS, UMR 5215 LPCNO, 135 avenue de Rangueil, 31077 Toulouse (France), Fax: (+33) 561-559-697
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  • Prof. Dr. Jun Okuda

    Corresponding author
    1. Institut für Anorganische Chemie, RWTH Aachen University, Landoltweg 1, 52056 Aachen (Germany), Fax: (+49) 241-80-92644
    • Institut für Anorganische Chemie, RWTH Aachen University, Landoltweg 1, 52056 Aachen (Germany), Fax: (+49) 241-80-92644
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Abstract

original image

Highly polar allylpotassium reacts with pyridine in a reversible 1,4-insertion to give an unstable N-metalated dihydropyridine (DHP). The N-metalated DHP can be stabilized by conversion into the corresponding potassium zincate or magnesate maintaining the reversible character of the insertion reaction (see scheme).

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