Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 19, Pages 4807-4811Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201402080
Keywords
bonding; carbenoids; catalysis; cyclopropanation; gold
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Funding
- MPG
- Fonds der Chemischen Industrie
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A formal gold-for-chromium transmetalation allowed the gold carbenoid species [Cy3PAuCAr2]NTf2 (11) (Ar=pMeOC(6)H(4)-) to be obtained in crystalline form. The structure in the solid state suggests that there is only little back donation of electron density from gold to the carbene center of 11 and hence very modest AuC double-bond character; rather, it is the organic ligand framework that is responsible for stabilizing this species by resonance delocalization of the accumulated positive charge. Because 11 is capable of cyclopropanating p-methoxystyrene even at low temperature, the discussion of its structure is deemed relevant for a better understanding of the mechanisms of -acid catalysis in general.
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