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Experimental evidence for the involvement of dinuclear alkynylcopper(I) complexes in alkyne-azide chemistry
journal contribution
posted on 2014-09-10, 13:16 authored by Benjamin BuckleyBenjamin Buckley, Sandie DannSandie Dann, Harry HeaneyDinuclear alkynylcopper(I) ladderane complexes are prepared by a robust and simple protocol involving the reduction of Cu2(OH)3OAc or Cu(OAc)2 by easily oxidised alcohols in the presence of terminal alkynes; they function as efficient catalysts in copper-catalysed alkyne–azide cycloaddition reactions as predicted by the Ahlquist–Fokin calculations. The same copper(I) catalysts are formed during reactions by using the Sharpless–Fokin protocol. The experimental results also provide evidence that sodium ascorbate functions as a base to deprotonate terminal alkynes and additionally give a convincing alternative explanation for the fact that the CuI-catalysed reactions of certain 1,3-diazides with phenylacetylene give bis(triazoles) as the major products. The same dinuclear alkynylcopper(I) complexes also function as catalysts in cycloaddition reactions of azides with 1-iodoalkynes.
Funding
This work was supported by Loughborough University. BRB thanks Research Councils UK for a RCUK Fellowship.
History
School
- Science
Department
- Chemistry
Published in
CHEMISTRY-A EUROPEAN JOURNALVolume
16Issue
21Pages
6278 - 6284 (7)Citation
BUCKLEY, B.R., DANN, S.E. and HEANEY, H., 2010. Experimental evidence for the involvement of dinuclear alkynylcopper(I) complexes in alkyne-azide chemistry. Chemistry - A European Journal, 16 (21), pp. 6278 - 6284.Publisher
© WILEY-VCH Verlag GmbH & Co.Version
- SMUR (Submitted Manuscript Under Review)
Publisher statement
This work is made available according to the conditions of the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) licence. Full details of this licence are available at: https://creativecommons.org/licenses/by-nc-nd/4.0/Publication date
2010Notes
Closed access.ISSN
0947-6539Publisher version
Language
- en