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Issue 14, 2013
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The Cu(i) catalyzed Meerwein reaction in aqueous solutions proceeds via a radical mechanism. The effect of several ligands

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Abstract

The effect of the ligands 2,5,8,11-tetramethyl-2,5,8,11-tetraaza-dodecane and fumarate on the mechanism and kinetics of the Cu(I) catalyzed Meerwein reaction was studied. The results point out that initially the Cu(I) ion binds to the aromatic ring with the diazo substituent. This reaction is followed by a redox process involving N2 loss and the formation of an aryl radical, R˙. The following kinetics depends on the nature of the ligand, its effect on the redox potential and the steric hindrance it induces on the central copper ion. Clearly the ligand 2,5,8,11-tetramethyl-2,5,8,11-tetraaza-dodecane does not form an optimal catalyst with Cu(I) while it does for the Ullmann reaction.

Graphical abstract: The Cu(i) catalyzed Meerwein reaction in aqueous solutions proceeds via a radical mechanism. The effect of several ligands

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Article information


Submitted
27 Oct 2012
Accepted
14 Jan 2013
First published
14 Jan 2013

Dalton Trans., 2013,42, 4985-4993
Article type
Paper

The Cu(I) catalyzed Meerwein reaction in aqueous solutions proceeds via a radical mechanism. The effect of several ligands

A. Burg, Y. Wolfer, H. Kornweitz, L. Shenar-Jackson, A. Masarwa and D. Meyerstein, Dalton Trans., 2013, 42, 4985
DOI: 10.1039/C3DT32573C

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