Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2010, Issue 10, Pages 1875-1884Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200901446
Keywords
Click chemistry; Cycloaddition; Alkynes; Azides; Copper; Nanoparticles
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Funding
- Spanish Ministerio de Educacion y Ciencia (MEC) [CTQ2007-65218, 2010-CSD2007-00006]
- Generalitat Valenciana [PROMETEO/2009/039]
- Secretaria General de Ciencia y Tecnologia (SeCyT)
- Universidad Nacional del Sur [PGI 24/Q014]
- Vicerrectorado de Investigacion, Desarrollo e Innovacion, Universidad de Alicante
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Readily prepared copper nanoparticles were found to catalyse the 1,3-dipolar cycloaddition of azides and alkynes up to rates comparable to those of microwave chemistry. Both the preparation of the nanoparticles and the click reaction are carried out under mild conditions, in short reaction times and in the absence of any stabilising additive or ligand. A *variety of 1,2,3-triazoles were prepared in excellent yields. A reaction mechanism was postulated on the basis of different reactivity studies and deuteration experiments. Copper(I) acetylides were demonstrated to be the real intermediate species.
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