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Synthesis of Ester‐ and Phosphonate‐Functionalized Au I –Imidazolylidene Chlorides through the Isonitrile Route
Author(s) -
Wurm Thomas,
Hornung Julius,
O'Neill Matthew,
Rudolph Matthias,
Rominger Frank,
Hashmi A. Stephen K.
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201700214
Subject(s) - phosphonate , chemistry , nucleophile , carbene , double bond , ring (chemistry) , amine gas treating , trimethylamine , combinatorial chemistry , polymer chemistry , medicinal chemistry , stereochemistry , organic chemistry , catalysis
Starting from DMSAuCl, isonitriles and functionalized propargylammonium salts in the presence of simple trimethylamine as auxiliary base, unsymmetrically substituted ester‐ and phosphonate‐functionalized Au I –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.