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Experimental evidence for the involvement of dinuclear alkynylcopper(I) complexes in alkyne-azide chemistry

journal contribution
posted on 10.09.2014 by Benjamin Buckley, Sandie Dann, Harry Heaney
Dinuclear 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 JOURNAL

Volume

16

Issue

21

Pages

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

2010

Notes

Closed access.

ISSN

0947-6539

Language

en

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