Molecular mechanism of acid-triggered aryl–halide reductive elimination in well-defined aryl–CuIII–halide species

Alicia Casitas; Albert Poater; Miquel Solà; Shannon S. Stahl; Miquel Costas; Xavi Ribas

doi:10.1039/C0DT00284D

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Molecular mechanism of acid-triggered aryl–halide reductive elimination in well-defined aryl–Cu^III–halide species†‡

Alicia Casitas,§^a Albert Poater,§^b Miquel Solà,*^ac Shannon S. Stahl,*^d Miquel Costas^a and Xavi Ribas*^a

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* Corresponding authors

^a Departament de Química, Universitat de Girona, Campus de Montilivi, Girona, Catalonia, Spain
E-mail: xavi.ribas@udg.edu
Fax: +34-972418150
Tel: +34-972419842

^b Catalan Institute for Water Research (ICRA), H2O Building, Scientific and Technological Park of the University of Girona, Emili Grahit 101, Girona, Catalonia, Spain

^c Institut de Química Computacional, Universitat de Girona, Campus Montilivi, Girona, Catalonia, Spain
E-mail: miquel.sola@udg.edu
Fax: +34-972418150
Tel: +34-972418912

^d Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, USA
E-mail: stahl@chem.wisc.edu
Fax: +1-608-262-6143
Tel: +1-608-265-6288

Abstract

Well-defined aryl–Cu^III–halide species undergo reductive elimination upon acid addition resulting in the formation of strong aryl–halide bonds. The computationally studied mechanism points towards ligand protonation as the rate-determining step, in agreement with previous experimental data.

This article is part of the themed collection: Dalton Discussion 12: Catalytic C–H and C–X bond activation (DD12)

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Supplementary files

Experimental details, Full computational details and xyz coordinates for all calculated species and HOMA indexes PDF (370K)

Article information

DOI: https://doi.org/10.1039/C0DT00284D
Article type: Paper
Submitted: 09 Apr 2010
Accepted: 25 May 2010
First published: 01 Oct 2010

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Dalton Trans., 2010,39, 10458-10463

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Molecular mechanism of acid-triggered aryl–halide reductive elimination in well-defined aryl–Cu^III–halide species

A. Casitas, A. Poater, M. Solà, S. S. Stahl, M. Costas and X. Ribas, Dalton Trans., 2010, 39, 10458 DOI: 10.1039/C0DT00284D

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Dalton Transactions