Heteroarylthiomethylsilanes. Synthesis and application to heteroarylthiomethylation of carbonyl compounds [1]

✍ Scribed by Makoto Hojo; Naruyasu Ishibashi; Akira Hosomi

• Book ID: 102846596
• Publisher: John Wiley and Sons
• Year: 1994
• Tongue: English
• Weight: 625 KB
• Volume: 5
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.520050307

✦ Synopsis

Heteroarylthiomethyltrimethylsilanes bearing a 2pyridyl, 2-imidazolyl, 5-tetrazolyl, or 2-pyrimidinyl group, readily prepared by the reaction of heteroarylmercaptans with habmethyltrimethylsilane in the presence of a base, are synthetic equivalents of heteroarylthiomethyl anions, otherwise inaccessible, and are effective reagents for the introduction of a heteroarylthiomethyl group at a carbonyl carbon atom in the presence of a catalytic amount of tetrabutylammonium fluoride.