1.
J Org Chem
; 88(21): 14969-14977, 2023 Nov 03.
Artigo
em Inglês
| MEDLINE
| ID: mdl-37862453
RESUMO
A new fluorinated azidoethaneâ1-azido-1,1,2,2-tetrafluoroethaneâwas prepared in quantitative yield by the addition of an azide anion to tetrafluoroethylene in a protic medium. The title azide was shown to be thermally stable and insensitive to impact. Copper(I)-catalyzed [3 + 2] cycloaddition with alkynes afforded 4-substituted N-tetrafluoroethyl-1,2,3-triazoles which underwent rhodium(II)-catalyzed transannulation with nitriles to novel N-tetrafluoroethylimidazoles or the reaction with triflic acid to enamido triflates. [3 + 2] Cycloaddition of the title azide with primary amines afforded novel 5-difluoromethyl tetrazoles.