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Chiral Transition‐Metal Complexes of Phenanthro‐Annulated N‐Heterocyclic Carbenes – Synthesis and Reactivity
Author(s) -
Mormul Jaroslaw,
Steimann Manfred,
MaichleMössmer Cäcilia,
Nagel Ulrich
Publication year - 2013
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201300061
Subject(s) - chemistry , carbene , transmetalation , deprotonation , imidazole , medicinal chemistry , reactivity (psychology) , alkylation , acetonitrile , transition metal , yield (engineering) , alkyl , transition metal carbene complex , organic chemistry , catalysis , ion , medicine , materials science , alternative medicine , pathology , metallurgy
A straightforward route to chiral Ag I and Ru II complexes with phenanthrene‐fused N‐heterocyclic carbene (NHC) ligands is described. The chiral imidazole derivative 1 was prepared in high yield by a simple one‐pot reaction starting from commercially available 9,10‐phenanthrenequinone. Imidazolium salts 2 and 3 were obtained by alkylation of 1 with alkyl bromides and subsequent anion exchange with Amberlyst A21 resin. Deprotonation with KO t Bu led to the corresponding free carbenes 4 and 5 , which were isolated without dimerization. Stirring carbene 4 in acetonitrile resulted in CH insertion. Ag I complexes were obtained by treatment of the imidazolium salts with Ag 2 O and showed an interesting low‐temperature behavior in the 1 H NMR spectrum. Transmetalation with a Ru precursor led to the corresponding Ru II complexes.
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