Lewis Acid Promoted Benzylic Cross-Couplings of Pyridines with Aryl Bromides

Authors

  • Dr. Stéphanie Duez,

    1. Department Chemie, Ludwig Maximilians-Universität München, Butenandtstrasse 5–13, Haus F, 81377 München (Germany)
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  • M. Sc. Andreas K. Steib,

    1. Department Chemie, Ludwig Maximilians-Universität München, Butenandtstrasse 5–13, Haus F, 81377 München (Germany)
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  • M. Sc. Sophia M. Manolikakes,

    1. Department Chemie, Ludwig Maximilians-Universität München, Butenandtstrasse 5–13, Haus F, 81377 München (Germany)
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  • Prof. Dr. Paul Knochel

    Corresponding author
    1. Department Chemie, Ludwig Maximilians-Universität München, Butenandtstrasse 5–13, Haus F, 81377 München (Germany)
    • Department Chemie, Ludwig Maximilians-Universität München, Butenandtstrasse 5–13, Haus F, 81377 München (Germany)
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  • We thank the Fonds der Chemischen Industrie, the European Research Council (ERC), and the Deutsche Forschungsgemeinschaft (DFG) for financial support. We also thank BASF AG (Ludwigshafen), Chemetall GmbH (Frankfurt), and Heraeas (Hanau) for generous gifts of chemicals.

Abstract

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Either ZnCl2, Sc(OTf)3 , or BF3⋅OEt2 can promote the palladium-catalyzed arylation of methylpyridines and related heterocycles (see example). The complexation of the Lewis acid to the nitrogen atom in the heterocycle facilitates the reductive elimination, leading to various arylated pyridines in high yields. BF3⋅OEt2 was also found to promote highly regioselective metalations in the case of 2,4-lutidine.

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