Nonafluorobutanesulfonyl Azide: A Shelf‐Stable Diazo Transfer Reagent for the Synthesis of Azides from Primary Amines

Abstract

Nonafluorobutanesulfonyl azide is an efficient, shelf-stable and cost-effective diazo transfer reagent for the synthesis of azides from primary amines. The reagent can also be successfully applied to the one-pot regioselective synthesis of 1,2,3-tri-A C H T U N G T R E N N U N G azoles from primary amines by a sequential diazo transfer and azide-alkyne 1,3-dipolar cycloaddition process catalyzed by copper. The cycloaddition step can be conducted in an inter-or intramolecular way to afford 1,4-or 1,5-disubstituted triazoles, respectively. The atypical 1,5-regioselectivity under copper catalysis is a consequence of geometrical constraints of the amino-alkyne substrates used in the intramolecular version. Nonafluorobutanesulfonyl azide offers an advantageous alternative to the better known and most commonly used trifluoromethanesulfonyl azide.

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