title: Synthesis of Ester- and Phosphonate-Functionalized AuI-Imidazolylidene Chlorides through the Isonitrile Route.
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.
authors.affiliation: Organisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
authors.forename: Thomas
authors.initials: T
authors.lastname: Wurm
authors.affiliation: Organisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
authors.forename: Julius
authors.initials: J
authors.lastname: Hornung
authors.affiliation: Organisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
authors.forename: Matthew
authors.initials: M
authors.lastname: O'Neill
authors.affiliation: Organisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
authors.forename: Matthias
authors.initials: M
authors.lastname: Rudolph
authors.affiliation: Organisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
authors.forename: Frank
authors.initials: F
authors.lastname: Rominger
authors.affiliation: Organisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.|Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah, 21589, Saudi Arabia.
authors.forename: A Stephen K
authors.identifier: http://orcid.org/0000-0002-6720-8602
authors.initials: AS
authors.lastname: Hashmi
keywords: N-heterocyclic carbene ligands; gold; isonitriles; template synthesis