C–C bond coupling between the organometallic cations CH3Ag2+, CH3Cu2+ and CH3AgCu+ and allyliodide

George N. Khairallah; Tom Waters; Richard A. J. O'Hair

doi:10.1039/B822371H

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C–C bond coupling between the organometallic cations CH₃Ag₂⁺, CH₃Cu₂⁺ and CH₃AgCu⁺ and allyliodide†

George N. Khairallah,^ab Tom Waters^ab and Richard A. J. O'Hair*^ab

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* Corresponding authors

^a School of Chemistry, University of Melbourne, Victoria, Australia
E-mail: rohair@unimelb.edu.au
Fax: +613 9347 5180
Tel: +61 3 8344 2452

^b Bio21 Institute of Molecular Science and Biotechnology, The University of Melbourne, Victoria, Australia

Abstract

Electrospray ionisation on a mixture of AgNO₃ (in MeOH/H₂O/acetic acid), (CH₃CO₂)₂Cu (in MeOH) and acetic acid (in MeOH) yields the metal carboxylate cations CH₃CO₂Ag₂⁺, CH₃CO₂AgCu⁺ and CH₃CO₂Cu₂⁺. Collision induced dissociation of these carboxylate cations yields the organometallic cations CH₃Ag₂⁺, CH₃AgCu⁺ and CH₃Cu₂⁺. The ion-molecule reactions of these organometallic cations with allyliodide were studied in a quadrupole ion trap mass spectrometer. C–C bond coupling occurred to yield the ionic products Ag₂I⁺, AgCuI⁺ and Cu₂I⁺. DFT calculations were carried out on these C–C bond coupling reactions. In all cases, the reactions are highly exothermic and involve initial coordination of the allyliodide to both metal atoms, with the iodine coordinating to one atom and the alkene moiety coordinating to the other. The overall mechanism of C–C bond coupling involves oxidative addition of the allyliodide followed by reductive elimination of 1-butene.

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Supplementary files

Cartesian coordinates for structures of ions and neutrals andFig. S1–S2 PDF (1445K)

Article information

DOI: https://doi.org/10.1039/B822371H
Article type: Paper
Submitted: 12 Dec 2008
Accepted: 13 Jan 2009
First published: 20 Feb 2009

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Dalton Trans., 2009, 2832-2836

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C–C bond coupling between the organometallic cations CH₃Ag₂⁺, CH₃Cu₂⁺ and CH₃AgCu⁺ and allyliodide

G. N. Khairallah, T. Waters and R. A. J. O'Hair, Dalton Trans., 2009, 2832 DOI: 10.1039/B822371H

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Dalton Transactions