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Steering the Surprisingly Modular π-Acceptor Properties of N-Heterocyclic Carbenes: Implications for Gold Catalysis

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  • Generous financial support by the MPG and the Fonds der Chemischen Industrie is gratefully acknowledged. We thank the NMR spectroscopy, X-ray crystallography, and chromatography departments of our institute for excellent support, K. Radkowski for the preparation of [6⋅AuCl], and Ch. Laurich, Max-Planck-Institut für Bioanorganische Chemie, Mülheim, for recording the electrochemical data.

Abstract

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Accept it! Although the π-acceptor properties of N-heterocyclic carbenes (NHCs) are often considered negligible, they can be enhanced to the extent that they start to dominate the catalytic behavior of gold–NHC complexes (see scheme). As it seems to be easier to tune the π acidity of NHCs than to alter their σ-donor properties, the general perception of this important class of ancillary ligands needs to be revised.

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Ancillary