Preparation of Solid Salt-Stabilized Functionalized Organozinc Compounds and their Application to Cross-Coupling and Carbonyl Addition Reactions

Authors

  • MSc. Sebastian Bernhardt,

    1. Ludwig Maximilians-Universität München, Department Chemie, Butenandtstrasse 5-13, Haus F, 81377 München (Germany)
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  • Dr. Georg Manolikakes,

    1. Johann Wolfgang Goethe-Universität Frankfurt, Institut für Organische Chemie und Chemische Biologie, Max-von-Laue-Strasse 7, 60438 Frankfurt am Main (Germany)
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  • MSc. Thomas Kunz,

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

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

Abstract

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Powdered organozinc reagents: Various aryl and heteroaryl bromides as well as benzylic chlorides react with Mg and Zn(OPiv)2⋅2 LiCl (OPiv=pivalate) to provide solid organozinc reagents after solvent evaporation. These powders can be stored at room temperature under argon for months and can be manipulated in air for a short time. They undergo smooth Negishi cross-coupling and carbonyl addition reactions (see scheme).

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