Journal
JOURNAL OF FLUORINE CHEMISTRY
Volume 109, Issue 2, Pages 173-181Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/S0022-1139(01)00390-6
Keywords
imidazole-N-difluoromethyltrimethyl-silane; 1-difluoromethyltrimethylsilyl-pyridinium triflate; N-difluoromethylide; N-trifluoromethyl-imidazole
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Reductive debromination of N-bromodifluoromethyl-4-dimethylaminopyridinium bromide. 1-bromodifluoromethyl-imidazole, 1-methyl-3-bromodifluoromethyl-imidazolium bromide and 1-bromodifluoromethyl-2-methyl-benzimidaz using tetrakis(dimelhylamino)ethylene (TDAE) or tris(diethylamido)phosphite leads to new fluorinated carbanionic species, namely heteroarylium-N-difluoromethylides and heteroaryl-N-difluoromethyl anions. In the presence of electrophiles such as benzaldehyde, chlorodiphenylphosphine and chlorotrimethylsilane, the corresponding heteroarylium- and heteroaryl-N-difluoromethylated derivatives, imidazole-N-difluoromethyl-phosphines and -silanes, 2-methyl-benzimidazole-N-difluoromethyltrimethyl-carbinols-phosphines and -silanes were obtained. Similar 4-dimethylaminopyridinium derivatives were synthesized, (C) 2001 Elsevier Science B.V. All rights reserved.
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