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Simple Synthetic Routes to N‐Heterocyclic Carbene Gold(I)–Aryl Complexes: Expanded Scope and Reactivity
Author(s) -
Tzouras Nikolaos V.,
Saab Marina,
Janssens Wim,
Cauwenbergh Thibault,
Van Hecke Kristof,
Nahra Fady,
Nolan Steven P.
Publication year - 2020
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.202000876
Subject(s) - synthon , carbene , reactivity (psychology) , chemistry , aryl , combinatorial chemistry , catalysis , reagent , organic chemistry , medicine , alkyl , alternative medicine , pathology
The discovery of sustainable and scalable synthetic protocols leading to gold–aryl compounds bearing N‐heterocyclic carbene (NHC) ligands sparked an investigation of their reactivity and potential utility as organometallic synthons. The use of a mild base and green solvents provide access to these compounds, starting from widely available boronic acids and various [Au(NHC)Cl] complexes, with reactions taking place under air, at room temperature and leading to high yields with unprecedented ease. One compound, ( N , N ′‐bis[2,6‐(di‐isopropyl)phenyl]imidazol‐2‐ylidene)(4‐methoxyphenyl)gold, ([Au(IPr)(4‐MeOC 6 H 4 )]), was synthesized on a multigram scale and used to gauge the reactivity of this class of compounds towards C−H/N−H bonds and with various acids, revealing simple pathways to gold–based species that possess attractive properties as materials, reagents and/or catalysts.