New In Situ Trapping Metalations of Functionalized Arenes and Heteroarenes with TMPLi in the Presence of ZnCl2 and Other Metal Salts |
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| Authors: | M?Sc Annette Frischmuth Dr Maitane Fernández M?Sc Nadja M Barl M?Sc Florian Achrainer Prof?Dr Hendrik Zipse Dr Guillaume Berionni Prof?Dr Herbert Mayr Prof?Dr Konstantin Karaghiosoff Prof?Dr Paul Knochel |
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| Affiliation: | Ludwig Maximilians‐Universit?t München, Department Chemie, Butenandtstrasse 5‐13, Haus F, 81377 München (Germany) |
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| 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. |
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| Keywords: | amide bases cross‐coupling metalation nitrogen heterocycles organometallic compounds |
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