Ruthenium(II)‐(Arene)‐N‐Heterocyclic Carbene Complexes: Efficient and Selective Catalysts for the N‐Alkylation of Aromatic Amines with Alcohols

A series of unsymmetrical 1,3‐disubstituted benzimidazolium chlorides were synthesized as N‐heterocyclic carbene (NHC) precursors. These compounds were used for synthesis of the new ruthenium(II) complexes of the type [RuCl2(arene)(NHC)], (arene = η6‐p‐cymene). The structures of all compounds were c...

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Bibliographic Details
Published in:European journal of inorganic chemistry 2019-06, Vol.2019 (21), p.2598-2606
Main Authors: Kaloğlu, Nazan, Achard, Mathieu, Bruneau, Christian, Özdemir, İsmail
Format: Article
Language:English
Subjects:
Alcohols
Alkylation
Amines
Aromatic amines
Borrowing hydrogen strategy
Carbene ligands
Catalysis
Catalytic activity
Chemical Sciences
Coordination chemistry
Homogeneous catalysis
Infrared spectroscopy
Inorganic chemistry
NMR
Nuclear magnetic resonance
Ruthenium
Ruthenium compounds
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Summary:A series of unsymmetrical 1,3‐disubstituted benzimidazolium chlorides were synthesized as N‐heterocyclic carbene (NHC) precursors. These compounds were used for synthesis of the new ruthenium(II) complexes of the type [RuCl2(arene)(NHC)], (arene = η6‐p‐cymene). The structures of all compounds were characterized by 1H NMR, 13C NMR and FT‐IR spectroscopy techniques. The catalytic activity of the ruthenium complexes has been evaluated with respect to the mono‐N‐alkylation reactions of aromatic amines with various alcohol derivatives under solvent‐free conditions at 120 °C using the borrowing hydrogen strategy. Five new ruthenium(II) complexes with general formula [RuCl2(NHC)(η6‐p‐cymene)], (NHC = N‐heterocyclic carbene) were synthesized. The obtained complexes were fully characterized by 1H NMR, 13C NMR, and FT‐IR spectroscopy. The catalytic activity of all ruthenium complexes have been evaluated in the N‐alkylation of anilines with alcohol derivatives using the borrowing hydrogen strategy.
ISSN:1434-1948
1099-0682
DOI:10.1002/ejic.201900191