Synthesis of ester- and phosphonate-functionalized auI-imidazolylidene chlorides through the isonitrile route

• Verfasst von: Wurm, Thomas [VerfasserIn]
• Verfasst von: Rudolph, Matthias [VerfasserIn]
• Verfasst von: Rominger, Frank [VerfasserIn]
• Verfasst von: Hashmi, A. Stephen K. [VerfasserIn]
• Titel: Synthesis of ester- and phosphonate-functionalized auI-imidazolylidene chlorides through the isonitrile route
• Verf.angabe: Thomas Wurm, Julius Hornung, Matthew O'Neill, Matthias Rudolph, Frank Rominger, A. Stephen K. Hashmi
• Umfang: 5 S.
• Fussnoten: Gesehen am 29.08.2017
• Titel Quelle: Enthalten in: Chemistry - a European journal
• Jahr Quelle: 2017
• Band/Heft Quelle: 23(2017), 21, S. 5143-5147
• ISSN Quelle: 1521-3765
• DOI: doi:10.1002/chem.201700214
• Datenträger: Online-Ressource
• Sprache: eng
• K10plus-PPN: 1562799592

Abstract

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.