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Issue 3, 2010
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Direct observation of CuI/CuIIIredox steps relevant to Ullmann-type coupling reactions

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Abstract

A series of aryl–copper(III)-halide complexes have been synthesized and characterized by NMR and UV-visible spectroscopy, cyclic voltammetry and X-ray crystallography. These complexes closely resemble elusive intermediates often invoked in catalytic reactions, such as Ullmann–Goldberg cross-coupling reactions, and their preparation has enabled direct observation and preliminary characterization of aryl halide reductive elimination from CuIII and oxidative addition to CuI centers. In situ spectroscopic studies (1H NMR, UV-visible) of a Cu-catalyzed C–N coupling reaction provides definitive evidence for the involvement of an aryl-copper(III)-halide intermediate in the catalytic mechanism. These results provide the first direct observation of the CuI/CuIII redox steps relevant to Ullmann-type coupling reactions.

Graphical abstract: Direct observation of CuI/CuIII redox steps relevant to Ullmann-type coupling reactions

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Article information


Submitted
31 Mar 2010
Accepted
15 Apr 2010
First published
15 Jun 2010

Chem. Sci., 2010,1, 326-330
Article type
Edge Article

Direct observation of CuI/CuIII redox steps relevant to Ullmann-type coupling reactions

A. Casitas, A. E. King, T. Parella, M. Costas, S. S. Stahl and X. Ribas, Chem. Sci., 2010, 1, 326
DOI: 10.1039/C0SC00245C

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