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Improved Air-Stable Solid Aromatic and Heterocyclic Zinc Reagents by Highly Selective Metalations for Negishi Cross-Couplings

Authors

  • Dr. Christos I. Stathakis,

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

    1. Ludwig-Maximilians-Universität München, Department Chemie, Butenandtstrasse 5–13, Haus F, 81377 München (Germany)
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  • B. Sc. Valentin Quint,

    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 SE (Ludwigshafen) and Chemetall GmbH (Frankfurt) for the generous gift of chemicals.

Abstract

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Directed metalation using TMPMgClLiCl (TMP=2,2,6,6-tetramethylpiperidide) and subsequent transmetalation with Zn(OPiv)2 leads to aryl and heteroaryl zinc pivalates. After solvent evaporation, easy-to-handle fine powders are obtained that retain most of their activity (>85 %) when exposed to air for 4 h. They smoothly undergo Negishi cross-couplings, and technical-grade solvents can be used without significant loss of yield.

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