Enamine-Mediated Azide-Ketone [3+2] Cycloaddition of Azidoperfluoroalkanes

Abstract

An effective synthesis of highly functionalized N-perfluoroalkyl-1,2,3-triazoles from azidoperfluoroalkanes has been achieved. In situ generated enamines readily participate in the azide-carbonyl [3 + 2] cycloaddition, providing a facile way to fully substituted triazole frameworks in good to excellent yields.

The synthetic value of these triazoles was shown in the synthesis of perfluorinated 1,5-disubstituted triazoles by hydrolysis and decarboxylation.

Keywords

• azides
• cycloaddition
• fluorine
• triazoles
• trifluoromethyl