D. Tichý, Vojtech Kostal, Vladimir A. Motornov
Aug 3, 2020
Citations
0
Influential Citations
15
Citations
Journal
The Journal of organic chemistry
Abstract
A straightforward synthesis of 1-azido-2-bromo-1,1,2,2-tetrafluoroethane on a multi-gram scale from 1,2-dibromotetrafluoroethane and sodium azide in a novel process initiated by organomagnesium compound (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 transannula-tion with nitriles to N-tetrafluoroethylated imidazoles and rhodium-catalyzed ring-opening and cyclization to N-difluoromethylated oxazoles and thiazoles.