Suarez JR, Trastoy Bello B, Perez-Ojeda Rodriguez ME, Marin-Barrios R, Chiara JL (2010)
Publication Status: Published
Publication Type: Journal article
Publication year: 2010
Publisher: WILEY-V C H VERLAG GMBH
Book Volume: 352
Pages Range: 2515-2520
Journal Issue: 14-15
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-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.
APA:
Suarez, J.R., Trastoy Bello, B., Perez-Ojeda Rodriguez, M.E., Marin-Barrios, R., & Chiara, J.L. (2010). Nonafluorobutanesulfonyl Azide: A Shelf-Stable Diazo Transfer Reagent for the Synthesis of Azides from Primary Amines. Advanced Synthesis & Catalysis, 352(14-15), 2515-2520. https://dx.doi.org/10.1002/adsc.201000417
MLA:
Suarez, Jose Ramon, et al. "Nonafluorobutanesulfonyl Azide: A Shelf-Stable Diazo Transfer Reagent for the Synthesis of Azides from Primary Amines." Advanced Synthesis & Catalysis 352.14-15 (2010): 2515-2520.
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