Preparation and Regioselective Magnesiation or Lithiation of Bis(trimethylsilyl)methyl‐Substituted Heteroaryls for the Generation of Highly Functionalized Heterocycles |
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| Authors: | Thomas Klatt Veronika Werner Dr Marina G Maximova Dr Dorian Didier Prof?Dr Yitzhak Apeloig Prof?Dr Paul Knochel |
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| Institution: | 1. Department Chemie, Ludwig‐Maximilians‐Universit?t München, Butenandtstrasse 5–13, Haus F, 81377 München (Germany), Fax: (+49)?89‐2180‐77680;2. S. A. Esenin Ryazan State University (Russia);3. Schulich Faculty of Chemistry and the Lise Meitner‐Minerva Center for Computational Quantum Chemistry, Technion‐Israel Institute of Technology, Technion City, Haifa 32000 (Israel) |
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| Abstract: | A wide range of bis(trimethylsilyl)methyl (BTSM)‐ substituted heteroaryl derivatives has been prepared by using Kumada–Corriu or Negishi cross‐coupling reactions. The regioselective lithiation or magnesiation of these building blocks bearing a bulky BTSM group by using magnesium or lithium 2,2,6,6‐tetramethylpiperidide bases followed by quenching reactions with different electrophiles provides various functionalized N‐, O‐, or S‐heterocycles. Furthermore, the BTSM group can then be converted into formyl, methyl, or styryl groups to give access to a variety of highly functionalized heteroaromatics. |
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| Keywords: | heterocycles magnesium metalation silyl reagents synthetic methods |
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