Issue 12, 2011
From the journal:

Chemical Science

Reactivity of NHC Au(i)–C σ-bonds with electrophiles. An investigation of their possible involvement in catalytic C–C bond formation†

Magnus T. Johnson,a   J. Marthinus Janse van Rensburg,a   Martin Axelsson,a   Mårten S. G. Ahlquist*b  and  Ola F. Wendt*a  

* Corresponding authors

a Centre for Analysis and Synthesis, Department of Chemistry, Lund University, P.O. Box 124, Lund, Sweden
E-mail: ola.wendt@organic.lu.se
Tel: +46 46 2228153

b Department of Theoretical Chemistry, School of Biotechnology, Royal Institute of Technology, Stockholm, Sweden
E-mail: mahlquist@theochem.kth.se

Abstract

The first example of the reaction of an isolated gold(I) complex with an aryl halide to form a C–C bond is reported. The reactivity of (NHC)Au(I)–R complexes towards a wide range of electrophiles was investigated. The Au–C σ-bond is shown to exhibit low nucleophilicity, but it is reactive towards MeI and MeOTf to form toluene, biphenyl and ethane, most likely through an oxidative mechanism. Carbon dioxide is completely unreactive. The experimental findings are supported by theoretical calculations.

Graphical abstract: Reactivity of NHC Au(i)–C σ-bonds with electrophiles. An investigation of their possible involvement in catalytic C–C bond formation

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Article information

DOI
https://doi.org/10.1039/C1SC00428J
Article type
Edge Article
Submitted
05 Jul 2011
Accepted
09 Sep 2011
First published
16 Sep 2011

Chem. Sci., 2011,2, 2373-2377

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Reactivity of NHC Au(I)–C σ-bonds with electrophiles. An investigation of their possible involvement in catalytic C–C bond formation

M. T. Johnson, J. Marthinus Janse van Rensburg, M. Axelsson, M. S. G. Ahlquist and O. F. Wendt, Chem. Sci., 2011, 2, 2373 DOI: 10.1039/C1SC00428J

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