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Preparation and Regioselective Metalation of Bis(trimethylsilyl)methyl‐Substituted Aryl Derivatives |
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| Authors: | Veronika Werner Thomas Klatt Masaya Fujii Jenifer Markiewicz Prof. Dr. Yitzhak Apeloig Prof. Dr. Paul Knochel |
| Affiliation: | 1. Department Chemie, Ludwig‐Maximilians‐Universit?t München, Butenandtstrasse 5‐13, Haus F, 81377 München (Germany);2. Graduate School of Pharmaceutical Sciences, University of Tokyo, 7‐3‐1, Hongo, Bunkyo‐ku, Tokyo 113‐0033 (Japan);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) |
| Abstract: | A range of bis(trimethylsilyl)methyl‐substituted aryl derivatives was prepared by using a Kumada–Corriu cross‐coupling reaction. The regioselective metalation of the resulting bis(trimethylsilyl)methyl‐substituted aryl derivatives bearing this bulky silyl group allowed the generation of functionalized aromatics. A regioselective switch in the presence or in the absence of the bis(trimethylsilyl)methyl group has been demonstrated. Furthermore, this silyl group was converted into a formyl group or a styryl group, enhancing the scope of application of such bis(trimethylsilyl)methyl‐substituted arenes. |
| Keywords: | aromatics lithiation magnesium metalation silyl reagents |