Experimental Evidence for the Involvement of Dinuclear Alkynylcopper(I) Complexes in Alkyne-Azide Chemistry

Autor:	Harry Heaney, Benjamin R. Buckley, Sandra E. Dann
Rok vydání:	2010
Předmět:	chemistry.chemical_classification Organic Chemistry Alkyne chemistry.chemical_element General Chemistry Copper Catalysis Cycloaddition chemistry.chemical_compound chemistry Phenylacetylene Polymer chemistry Click chemistry Organic chemistry Ladderane Azide
Zdroj:	Chemistry - A European Journal. 16:6278-6284
ISSN:	1521-3765 0947-6539
DOI:	10.1002/chem.201000447
Popis:	Dinuclear alkynylcopper(I) ladderane complexes are prepared by a robust and simple protocol involving the reduction of Cu(2)(OH)(3)OAc 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 Cu(I)-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.
Databáze:	OpenAIRE
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