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; J. Marthinus Janse van Rensburg; Martin Axelsson; Mårten S. G. Ahlquist; Ola F. Wendt

doi:10.1039/C1SC00428J

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Chemical Science

Issue 12, 2011

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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

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

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

DOI: 10.1039/C1SC00428J
Received 05 Jul 2011, Accepted 09 Sep 2011
First published on the web 16 Sep 2011

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Abstract
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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.

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Magnus T. Johnson
J. Marthinus Janse van Rensburg
Martin Axelsson
Mårten S. G. Ahlquist
Ola F. Wendt

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Chemical Science

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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