Differentiating C[BOND]Br and C[BOND]Cl Bond Activation by Using Solvent Polarity: Applications to Orthogonal Alkyl–Alkyl Negishi Reactions

Authors

  • Dr. Niloufar Hadei,

    1. Department of Chemistry, York University, 4700 Keele Street, Toronto, Ontario M3J 1P3 (Canada), Fax: (+1) 416-736-5936
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  • George T. Achonduh,

    1. Department of Chemistry, York University, 4700 Keele Street, Toronto, Ontario M3J 1P3 (Canada), Fax: (+1) 416-736-5936
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  • Dr. Cory Valente,

    1. Department of Chemistry, York University, 4700 Keele Street, Toronto, Ontario M3J 1P3 (Canada), Fax: (+1) 416-736-5936
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  • Dr. Christopher J. O'Brien,

    1. Department of Chemistry, York University, 4700 Keele Street, Toronto, Ontario M3J 1P3 (Canada), Fax: (+1) 416-736-5936
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  • Prof. Michael G. Organ

    Corresponding author
    1. Department of Chemistry, York University, 4700 Keele Street, Toronto, Ontario M3J 1P3 (Canada), Fax: (+1) 416-736-5936
    • Department of Chemistry, York University, 4700 Keele Street, Toronto, Ontario M3J 1P3 (Canada), Fax: (+1) 416-736-5936===

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  • This work was supported by NSERC (Canada) and the ORDCF (Ontario).

Abstract

original image

Alles in einen Topf: In der Negishi-Alkyl-Alkyl-Kreuzkupplung kann eine CAlkyl-Cl-Bindung „inaktiv“ oder „aktiv“ gesetzt werden, indem man einfach die Lösungsmittelpolarität ändert (siehe Schema). Mithilfe einer Umstellung des Lösungsmittelverhältnisses Dimethylimidazolidinon/Tetrahydrofuran von 1:2 auf 2:1 lassen sich orthogonale Kreuzkupplungen an difunktionellen Bromchloralkanen in einer Eintopfprozedur bei Raumtemperatur durchführen.

Ancillary