A novel type of nucleophilic substitution reactions on nonactivated aromatic compounds and benzene itself with trimethylsiliconide anions |
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Authors: | Postigo A Rossi R A |
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Institution: | INFIQC, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Córdoba 5000, Argentina. |
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Abstract: | reaction: see text]. The reaction of fluorobenzene with Me3Si- anion (1) in HMPA at room temperature surprisingly affords o- and p-fluorotrimethylsilylbenzenes (substitution of aromatic H for TMS, 76% yield) 7a and 7b and also 14% of trimethylsilylbenzene (2). Benzene itself reacts at 50 degrees C to furnish 4 in 45% yield. Pyridine affords p-trimethylsilylpyridine quantitatively. Mechanistic studies are presented. |
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