Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 17, Pages 11482-11489Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c01610
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Funding
- Czech Academy of Sciences [RVO: 61388963]
- Ministry of Education, Youth and Sports in the program INTEREXCELLENCE [LTAUSA18037]
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A straightforward synthesis of 1-azido-2-bromo-1,1,2,2-tetrafluoroethane on a multigram scale from 1,2-dibromote-trafluoroethane and sodium azide in a novel process initiated by organomagnesium compounds (i-PrMgCl center dot 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-allcyne cyclo- addition 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.
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