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


  • Dedicated to Prof. Adrian Gibbs Brook on the occasion of his seventieth birthday.


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