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A CuI/CuIII prototypical organometallic mechanism for the deactivation of an active pincer-like CuI catalyst in Ullmann-type couplings

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Abstract

Unraveling the mechanistic details of copper-catalyzed arylation of nucleophiles (Ullmann-type couplings) is a very challenging task. It is a matter of intense debate whether it is a radical-based process or an organometallic redox-based process. The ancillary ligand choice in Ullmann-type couplings plays a key role in such transformations and can strongly influence the catalytic efficiency as well as the mechanism. Here, we show how a predesigned tridentate pincer-like catalyst undergoes a deactivation pathway through a CuI/CuIII prototypical mechanism as demonstrated by helium-tagging infrared photodissociation (IRPD) spectroscopy and DFT studies, lending a strong support to the existence of an aryl–CuIII species in the Ullmann couplings using this tridentate ligand.

Graphical abstract: A CuI/CuIII prototypical organometallic mechanism for the deactivation of an active pincer-like CuI catalyst in Ullmann-type couplings

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Publication details

The article was received on 09 Jun 2017, accepted on 13 Jul 2017 and first published on 13 Jul 2017


Article type: Communication
DOI: 10.1039/C7CC04491G
Citation: Chem. Commun., 2017, Advance Article
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    A CuI/CuIII prototypical organometallic mechanism for the deactivation of an active pincer-like CuI catalyst in Ullmann-type couplings

    M. Rovira, L. Jašíková, E. Andris, F. Acuña-Parés, M. Soler, I. Güell, M. Wang, L. Gómez, J. M. Luis, J. Roithová and X. Ribas, Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7CC04491G

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