A straightforward synthesis of 1-azido-2-bromo-1,1,2,2-tetrafluoroethane on a multigram scale from 1,2-dibromotetrafluoroethane and sodium azide in a novel process initiated by organomagnesium compounds (i-PrMgCl·LiCl, turbo Grignard) is reported. Synthetic utility of the title azide in the preparation of N-tetrafluoroethylated and N-difluoromethylated five-membered nitrogen heterocycles was demonstrated with azide-alkyne cycloaddition to N-bromotetrafluoroethyl 1,2,3-triazoles, subsequent reduction to N-tetrafluoroethyl triazoles, rhodium-catalyzed transannulation with nitriles to N-tetrafluoroethylated imidazoles and rhodium-catalyzed ring-opening, and cyclization to N-difluoromethylated oxazoles and thiazoles.

Department of Organic Chemistry Faculty of Science Charles University Hlavova 2030 8 128 43 Prague Czech Republic

Higher Chemical College D 1 Mendeleev University of the Chemical Technology of Russia Miusskaya sq 9 125047 Moscow Russian Federation

Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences Flemingovo nam 2 166 10 Prague 6 Czech Republic

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Synthesis and Cycloaddition Reactions of 1-Azido-1,1,2,2-tetrafluoroethane

Synthesis of N-perfluoroalkyl-3,4-disubstituted pyrroles by rhodium-catalyzed transannulation of N-fluoroalkyl-1,2,3-triazoles with terminal alkynes