Please use this identifier to cite or link to this item: http://hdl.handle.net/10261/31023
Share/Export:
logo share SHARE logo core CORE BASE
Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL | DATACITE
Title

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

AuthorsSuárez, José Ramón; Trastoy, Beatriz ORCID; Pérez-Ojeda, M. Eugenia CSIC; Marín-Barrios, Rubén; Chiara, José Luis CSIC ORCID
KeywordsAmines
Azides
Click chemistry
Copper
Diazo transfer
Issue Date2010
PublisherWiley-Blackwell
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
URIhttp://hdl.handle.net/10261/31023
DOI10.1002/adsc.201000417
ISSN1615-4150
Appears in Collections:(IQOG) Artículos
(IQFR) Artículos

Files in This Item:
File Description SizeFormat
Full_paper_submitted_28_05_10.pdf290,2 kBAdobe PDFThumbnail
View/Open
Supporting_Information.pdf8,78 MBAdobe PDFThumbnail
View/Open
Show full item record
Review this work

SCOPUSTM   
Citations

47
checked on May 21, 2022

WEB OF SCIENCETM
Citations

47
checked on May 22, 2022

Page view(s)

394
checked on May 22, 2022

Download(s)

543
checked on May 22, 2022

Google ScholarTM

Check

Altmetric

Dimensions


WARNING: Items in Digital.CSIC are protected by copyright, with all rights reserved, unless otherwise indicated.