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  Gold Carbenoids: Lessons Learnt from a Transmetalation Approach

Seidel, G., Gabor, B., Goddard, R., Heggen, B., Thiel, W., & Fürstner, A. (2014). Gold Carbenoids: Lessons Learnt from a Transmetalation Approach. Angewandte Chemie International Edition, 53(3), 879-882. doi:10.1002/anie.201308842.

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anie_201308842_sm_miscellaneous_information.pdf (Supplementary material), 2MB
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anie_201308842_sm_miscellaneous_information.pdf
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Copyright Date:
2013
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Wiley-VCH 69451 Weinheim, Germany
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 Creators:
Seidel, Günter1, Author              
Gabor, Barbara2, Author              
Goddard, Richard3, Author              
Heggen, Berit4, Author              
Thiel, Walter4, Author              
Fürstner, Alois1, Author              
Affiliations:
1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              
2Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445623              
3Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445625              
4Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445590              

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Free keywords: carbene complexes; chromium; dimetalation; gold; tungsten
 Abstract: Carbophilic catalysts that are based on AuI allow a host of different nucleophiles to be added across various π systems.1–3 Although many of these reactions are thought to proceed via gold carbenoids, the challenge to observe and characterize these putative intermediates has basically been unmet.4 The current mechanistic interpretation therefore largely relies on indirect evidence and computational data, some of which are subject to debate.5 In an attempt to fill this gap, we pursued a potential route to gold carbenoids by formal transmetalation of chromium or tungsten Fischer carbene complexes with [LAu]+. Whereas this transformation proceeds with exceptional ease as long as a stabilizing heteroelement is present on the carbene center, it stops half-way in its absence. Rather unusual bimetallic arrays are formed, which allow the charge density to delocalize over several positions. The obvious difficulty of releasing an “unstabilized” gold carbenoid has potential mechanistic implications for the understanding of π-acid catalysis in general.

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Language(s): eng - English
 Dates: 2013-10-102013-11-272014-01-13
 Publication Status: Published in print
 Pages: 4
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.201308842
 Degree: -

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Title: Angewandte Chemie International Edition
  Other : Angew. Chem., Int. Ed.
  Other : Angew. Chem. Int. Ed.
  Other : Angewandte Chemie, International Edition
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: 4 Volume / Issue: 53 (3) Sequence Number: - Start / End Page: 879 - 882 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851