Synthesis of ester- and phosphonate-functionalized auI-imidazolylidene chlorides through the isonitrile route
Starting from DMSAuCl, isonitriles and functionalized propargylammonium salts in the presence of simple trimethylamine as auxiliary base, unsymmetrically substituted ester- and phosphonate-functionalized AuI-imidazolylidene complexes were synthesized in an easy-to-use modular one-pot template synthe...
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| Main Authors: | , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
27 March 2017
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| In: |
Chemistry - a European journal
Year: 2017, Volume: 23, Issue: 21, Pages: 5143-5147 |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.201700214 |
| Online Access: | Verlag, Volltext: http://dx.doi.org/10.1002/chem.201700214 Verlag, Volltext: http://onlinelibrary.wiley.com/doi/10.1002/chem.201700214/epdf Verlag, Volltext: http://onlinelibrary.wiley.com/doi/10.1002/chem.201700214/abstract 
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| Author Notes: | Thomas Wurm, Julius Hornung, Matthew O'Neill, Matthias Rudolph, Frank Rominger, A. Stephen K. Hashmi |
| Summary: | Starting from DMSAuCl, isonitriles and functionalized propargylammonium salts in the presence of simple trimethylamine as auxiliary base, unsymmetrically substituted ester- and phosphonate-functionalized AuI-imidazolylidene complexes were synthesized in an easy-to-use modular one-pot template synthesis. In the course of the reaction, after the initial nucleophilic addition of the amine to the gold(I)-activated isonitrile, a Michael addition closes the N-heterocyclic carbene (NHC) ring. Then the remaining double bond migrates into the NHC ring, evidently a more stable position than the initial exocyclic double bond. These functional groups attached to the back bone of the NHC ligands represent ideal handles for a further modification of the system, for example an attachment to larger assemblies or heterogenization by an attachment to surfaces are conceivable. |
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| Item Description: | Gesehen am 29.08.2017 |
| Physical Description: | Online Resource |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.201700214 |