Study of Copper(I) Catalysts for the Synthesis of Carbanucleosides via Azide-Alkyne 1,3-Dipolar Cycloaddition

Julie Broggi; Silvia Díez-González; Jeffrey L. Petersen; Sabine Berteina-Raboin; Steven P. Nolan; Luigi A. Agrofoglio

doi:10.1055/s-2007-990943

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Synthesis 2008(1): 141-148
DOI: 10.1055/s-2007-990943

FEATUREARTICLE

Study of Copper(I) Catalysts for the Synthesis of Carbanucleosides via Azide-Alkyne 1,3-Dipolar Cycloaddition

Julie Broggi^a, Silvia Díez-González^b, Jeffrey L. Petersen^c, Sabine Berteina-Raboin^a, Steven P. Nolan*^b, Luigi A. Agrofoglio*^a
^a Institut de Chimie Organique et Analytique, UMR 6005, Université d’Orléans, 45067 Orléans, France
Fax: +33(2)38417281; e-Mail: luigi.agrofoglio@univ-orleans.fr;
^b Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans, 16, 43007 Tarragona, Spain
^c C. Eugene Bennet Department of Chemistry, West Virginia University, Morgantown, WV 26506-6045, USA

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Publication History

Received 22 October 2007
Publication Date:
07 December 2007 (online)

Abstract
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Abstract

The activity of three copper(I)-based catalytic systems in the preparation of various 1,2,3-triazolyl-carbanucleosides via the Huisgen azide-alkyne 1,3-dipolar cycloaddition is presented. The influence of the alkyne substituent, solvent, and heating mode were studied. The preparation of [1,2-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene]bromocopper [(IMes)CuBr] is discussed.

Key words

copper(I) catalysts - Huisgen 1,3-dipolar cycloaddition - carbanucleosides - N-heterocyclic carbenes

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File CCDC 654537 contains the complete crystallographic data for (IMes)CuBr. These data can be obtained free of charge from The Cambridge Crystallographic Data center via www.ccdc.cam.ac.uk/data-request/cif.

31

Ratio 1,4-triazole/1,5-triazole = 65:35.