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Molecules 2018, 23(3), 647; https://doi.org/10.3390/molecules23030647

Ruthenium(η61-arene-CH2-NHC) Catalysts for Direct Arylation of 2-Phenylpyridine with (Hetero)Aryl Chlorides in Water

1
Department of Chemistry, Faculty of Science and Arts, İnönü University, 44280 Malatya, Turkey
2
Catalysis Research and Application Center, İnönü University, 44280 Malatya, Turkey
3
Faculty of Arts and Science, Department of Chemistry, Mersin University, 33343 Mersin, Turkey
4
Institut des Sciences Chimiques de Rennes, Université de Rennes 1, 35042 Rennes, France
*
Author to whom correspondence should be addressed.
Received: 16 February 2018 / Revised: 7 March 2018 / Accepted: 7 March 2018 / Published: 13 March 2018
(This article belongs to the Special Issue Organometallic Catalysis in Organic Synthesis)
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Abstract

A series of new benzimidazolium halides were synthesized in good yields as unsymmetrical N-heterocyclic carbene (NHC) precursors containing the N–CH2–arene group. The benzimidazolium halides were readily converted into ruthenium(II)–NHC complexes with the general formula [RuCl261–arene–CH2–NHC)]. The structures of all new compounds were characterized by 1H NMR (Nuclear Magnetic Resonance), 13C NMR, FT-IR (Fourier Transform Infrared) spectroscopy and elemental analysis techniques. The single crystal structure of one benzimidazole ruthenium complex, 2b, was determined. The complex is best thought of as containing an octahedrally coordinated Ru center with the arene residue occupying three sites, the remaining sites being occupied by a (carbene)C–Ru bond and two Ru–Cl bonds. The catalytic activity of [RuCl261–arene–CH2–NHC)] complexes was evaluated in the direct (hetero)arylation of 2-phenylpyridine with (hetero)aryl chlorides in water as the nontoxic reaction medium. These results show that catalysts 2a and 2b were the best for monoarylation with simple phenyl and tolyl chlorides. For functional aryl chlorides, 2d, 2e, and 2c appeared to be the most efficient. View Full-Text
Keywords: homogeneous catalysis; ruthenium; N-heterocyclic carbene; 2-phenylpyridine; direct arylation; single crystal structure homogeneous catalysis; ruthenium; N-heterocyclic carbene; 2-phenylpyridine; direct arylation; single crystal structure
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Kaloğlu, N.; Özdemir, İ.; Gürbüz, N.; Arslan, H.; Dixneuf, P.H. Ruthenium(η61-arene-CH2-NHC) Catalysts for Direct Arylation of 2-Phenylpyridine with (Hetero)Aryl Chlorides in Water. Molecules 2018, 23, 647.

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