1.
J Org Chem
; 85(17): 11482-11489, 2020 09 04.
Artigo
em Inglês
| MEDLINE
| ID: mdl-32786641
RESUMO
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.