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Cobalt-Catalyzed C4-Selective Direct Alkylation of Pyridines

Authors

  • Dr. Takashi Andou,

    1. Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
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    • These authors contributed equally to this work.

  • Yutaka Saga,

    1. Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
    2. JST, ERATO, Kanai Life Science Catalysis Project, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
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    • These authors contributed equally to this work.

  • Hirotomo Komai,

    1. Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
    2. JST, ERATO, Kanai Life Science Catalysis Project, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
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  • Dr. Shigeki Matsunaga,

    Corresponding author
    1. Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
    2. JST, ACT-C, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
    • Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)

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  • Prof. Dr. Motomu Kanai

    Corresponding author
    1. Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
    2. JST, ERATO, Kanai Life Science Catalysis Project, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
    • Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)

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  • We thank Mr. Shohei Yamamoto for fruitful discussions and experimental support. This work was supported in part by ERATO from JST (M.K.), a Grant-in-Aid for Scientific Research on Innovative Areas “Molecular Activation Directed toward Straightforward Synthesis” from MEXT (S.M.), the ACT-C program from JST (S.M.) and the Naito Foundation. T.A. thanks JSPS for a postdoctoral fellowship.

Abstract

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Pyridine mit Anhang: Ein neuer Katalysator für die atomökonomische C4-selektive direkte Alkylierung von Pyridinen wird beschrieben. Eine Kombination aus CoBr2 und LiBEt3H katalysiert die Reaktion von Pyridinen mit 1-Alkenen bei 70 °C und ergibt die Alkylierungsprodukte mit C4/C2-Verhältnissen von >20:1. Substrat/Katalysator-Verhältnisse bis zu 4000 und eine Umsatzzahl von 3440 wurden erreicht.

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