A novel type of nucleophilic substitution reactions on nonactivated aromatic compounds and benzene itself with trimethylsiliconide anions

Authors
Postigo, A Rossi, RA
Citation
A. Postigo et Ra. Rossi, A novel type of nucleophilic substitution reactions on nonactivated aromatic compounds and benzene itself with trimethylsiliconide anions, ORG LETT, 3(8), 2001, pp. 1197-1200
Citations number
33
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
8
Year of publication
2001
Pages
1197 - 1200
Database
ISI
SICI code
1523-7060(20010419)3:8<1197:ANTONS>2.0.ZU;2-#
Abstract
The reaction of fluorobenzene with Me3Si- anion (1) in HMPA at room tempera ture surprisingly affords o- and p-fluorotrimethylsilylbenzenes (substituti on of aromatic H for TMS, 76% yield) 7a and 7b and also 14% of trimethylsil ylbenzene (2). Benzene itself reacts at 50 degreesC to furnish 4 in 45% yie ld. Pyridine affords p-trimethylsilylpyridine quantitatively. Mechanistic s tudies are presented.