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Title: | Nonafluorobutanesulfonyl Azide: A Shelf-Stable Diazo Transfer Reagent for the Synthesis of Azides from Primary Amines |
Authors: | Suárez, José Ramón; Trastoy, Beatriz ORCID; Pérez-Ojeda, M. Eugenia CSIC; Marín-Barrios, Rubén; Chiara, José Luis CSIC ORCID | Keywords: | Amines Azides Click chemistry Copper Diazo transfer |
Issue Date: | 2010 | Publisher: | Wiley-Blackwell | Citation: | Advanced Synthesis and Catalysis 352(14-15): 2515-2520 (2010) | 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-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. | Description: | 6 páginas, 2 esquemas, 2 tablas | Publisher version (URL): | http://dx.doi.org/10.1002/adsc.201000417 | URI: | http://hdl.handle.net/10261/31023 | DOI: | 10.1002/adsc.201000417 | ISSN: | 1615-4150 |
Appears in Collections: | (IQOG) Artículos (IQFR) Artículos |
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Full_paper_submitted_28_05_10.pdf | 290,2 kB | Adobe PDF | ![]() View/Open | |
Supporting_Information.pdf | 8,78 MB | Adobe PDF | ![]() View/Open |
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