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Highly Regioselective Preparation of Heteroaryl–Magnesium Reagents by Using a Br/Mg Exchange

Authors

  • Christoph Sämann,

    1. Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5–13, Haus F, 81377 München (Germany), Fax: (+49) 89-2180-77680
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  • Dr. Benjamin Haag,

    1. Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5–13, Haus F, 81377 München (Germany), Fax: (+49) 89-2180-77680
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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), Fax: (+49) 89-2180-77680
    • Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5–13, Haus F, 81377 München (Germany), Fax: (+49) 89-2180-77680
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Abstract

Disubstituted thienyl-, furyl- and pyridylmagnesium derivatives are regioselectively prepared from a Br/Mg exchange of the corresponding dibromo compounds by using either iPrMgClLiCl or hindered arylmagnesium reagents, such as isitylmagnesium bromidelithium chloride (isityl=2,4,6-triisopropyl-phenyl) complexed with a diamine ligand, in difficult cases. The selective functionalisations of these heterocyclic scaffolds by using Negishi cross-coupling reactions, acylations or addition to aldehydes were readily achieved.

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