Publication
547
J. Fluorine
Chem., 109 (2), 173-181, 2001
DOI: 10.1016/S0022-1139(01)00390-6 |
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Generation of heteroarylium-N-difluoromethylides and heteroaryl-N-difluoromethyl anions and their reactions with electrophiles: heteroaryl- and heteroarylium-N-difluoromethyl trimethylsilanes and a new heteroaryl-N-trifluoromethane
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German Bissky,
Gerd-Volker Röschenthaler, Enno
Lork, Jan Barten, Maurice
Médebielle,
Vasilij Staninets and Alexander A. Kolomeitsev
Institute of Inorganic and Physical
Chemistry, University of Bremen, Leobener Strasse,
28334 Bremen, Germany, Electrochimie
Moléculaire, Université Paris7-Denis
Diderot, UMR CNRS 7591, Case Courrier 7107, 2 place Jussieu, F-75251 Paris Cedex
05, France and Institute of Organic Chemistry, Ukrainian Academy
of Sciences, Murmanskaya 5, 02094 Kiev, Ukraine
Reductive debromination of N-bromodifluoromethyl-4-dimethylaminopyridinium
bromide, 1-bromodifluoromethyl-imidazole, 1-methyl-3-bromodifluoromethyl-imidazolium
bromide and 1-bromodifluoromethyl-2-methyl-benzimidazole
using tetrakis(dimethylamino)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. |
