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Frischmuth A, Fernández M, Barl NM, et al. New in situ trapping metalations of functionalized arenes and heteroarenes with TMPLi in the presence of ZnCl2 and other metal salts. Angew Chem Int Ed Engl. 2014;53(30):7928-32doi: 10.1002/anie.201403688.
Frischmuth, A., Fernández, M., Barl, N. M., Achrainer, F., Zipse, H., Berionni, G., Mayr, H., Karaghiosoff, K., & Knochel, P. (2014). New in situ trapping metalations of functionalized arenes and heteroarenes with TMPLi in the presence of ZnCl2 and other metal salts. Angewandte Chemie (International ed. in English), 53(30), 7928-32. https://doi.org/10.1002/anie.201403688
Frischmuth, Annette, et al. "New in situ trapping metalations of functionalized arenes and heteroarenes with TMPLi in the presence of ZnCl2 and other metal salts." Angewandte Chemie (International ed. in English) vol. 53,30 (2014): 7928-32. doi: https://doi.org/10.1002/anie.201403688
Frischmuth A, Fernández M, Barl NM, Achrainer F, Zipse H, Berionni G, Mayr H, Karaghiosoff K, Knochel P. New in situ trapping metalations of functionalized arenes and heteroarenes with TMPLi in the presence of ZnCl2 and other metal salts. Angew Chem Int Ed Engl. 2014 Jul 21;53(30):7928-32. doi: 10.1002/anie.201403688. Epub 2014 Jun 12. PMID: 24923789.
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Angew Chem Int Ed Engl. 2014 Jul 21;53(30):7928-32. doi: 10.1002/anie.201403688. Epub 2014 Jun 12.

New in situ trapping metalations of functionalized arenes and heteroarenes with TMPLi in the presence of ZnCl2 and other metal salts.

Angewandte Chemie (International ed. in English)

Annette Frischmuth, Maitane Fernández, Nadja M Barl, Florian Achrainer, Hendrik Zipse, Guillaume Berionni, Herbert Mayr, Konstantin Karaghiosoff, Paul Knochel

Affiliations

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

PMID: 24923789 DOI: 10.1002/anie.201403688

Abstract

The addition of TMPLi to a mixture of an aromatic or heteroaromatic substrate with a metal salt such as MgCl2, ZnCl2, or CuCN at -78 °C first leads to lithiation of the arene followed by transmetalation with the metal salt to afford functionalized organometallic compounds of Mg, Zn, or Cu. This in situ trapping method allows an expedited metalation (-78 °C, 5 min) of a range of sensitive pyridines (bearing a nitro, ester, or cyano group) and allows the preparation of kinetic regioisomers of functionalized aromatic compounds or heterocycles not otherwise available by standard metalating agents, such as TMPMgCl⋅LiCl or TMPZnCl⋅LiCl.

© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: amide bases; cross-coupling; metalation; nitrogen heterocycles; organometallic compounds

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