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

AuthorsSuárez, José Ramón; Trastoy, Beatriz ; Pérez-Ojeda, M. Eugenia ; Marín-Barrios, Rubén; Chiara, José Luis
Click chemistry
Diazo transfer
Issue Date2010
CitationAdvanced Synthesis and Catalysis 352(14-15): 2515-2520 (2010)
AbstractNonafluorobutanesulfonyl 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-triazoles 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.
Description6 páginas, 2 esquemas, 2 tablas
Publisher version (URL)http://dx.doi.org/10.1002/adsc.201000417
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