Hypodentate coordination of N,N-di(alkyl/aryl)-N′-acylthiourea derivatives in Cu(I) complexes

Gunasekaran, N.; Ng, Seik Weng; Tiekink, Edward R. T.; Karvembu, Ramasamy

doi:10.1016/j.poly.2011.12.002

Cited by 29 publications

(22 citation statements)

References 35 publications

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“…43 Whereas the present catalytic system exhibited 56-98% conversion and 77-99% ee. L-Prolinate with [RuCl 2 (η 6 -benzene)] 2 as catalyst showed only 74% conversion and 45% ee, 37 which is inferior to our catalysts (1)(2)(3)(4)(5)(6). [(η 6benzene) Ru(biotinylated ligand)Cl] with an artificial metalloenzyme [(strept)avidin] showed 30% conversion and 63% ee.…”

Section: Asymmetric Transfer Hydrogenation Of Ketonescontrasting

confidence: 60%

“…52 The air stable half-sandwich Ru(II) complexes (1)(2)(3)(4)(5)(6) were prepared as orange solids in high yields (80-88%) from the reactions between [RuCl 2 (η 6 - 52 The air stable half-sandwich Ru(II) complexes (1)(2)(3)(4)(5)(6) were prepared as orange solids in high yields (80-88%) from the reactions between [RuCl 2 (η 6 - …”

Section: Synthesis Of Ru(ii)-benzene Complexesmentioning

confidence: 99%

“…[1][2][3][4][5][6][7][8][9] Half sandwich Ru(II) complexes having η 6 -p-cymene or η 6 -benzene unit are of recent interest due to their superior catalytic activities. [1][2][3][4][5][6][7][8][9] Half sandwich Ru(II) complexes having η 6 -p-cymene or η 6 -benzene unit are of recent interest due to their superior catalytic activities.…”

Section: Introductionmentioning

confidence: 99%

“…48 Pharmaceuticals which require chiral alcohols for their synthesis are antihypertensive, antiarrhythmic, anticholesterol and antiviral drugs, calcium and potassium channel blocking drugs and β 3 -receptor agonists. 51 In the present paper, we report the synthesis of the new Ru-benzene complexes, [RuCl 2 (η 6 -C 6 H 6 )L] (1-6), from [RuCl 2 (η 6 -C 6 H 6 )] 2 (1)(2)(3)(4)(5)(6) for ATH of ketones to their corresponding chiral alcohols is investigated and compared with similar η 6 -p-cymene complexes. 50 ATH of prochiral ketones is one of the powerful methods for the production of optically active secondary alcohols.…”

Section: Introductionmentioning

confidence: 99%

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Half-sandwich Ru(η⁶-C₆H₆) complexes with chiral aroylthioureas for enhanced asymmetric transfer hydrogenation of ketones – experimental and theoretical studies

Sheeba

Preethi

Nijamudheen

et al. 2015

Catal. Sci. Technol.

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The reactions of [RuCl 2 (η 6 -C 6 H 6 )] 2 with chiral aroylthiourea ligands yielded pseudo octahedral half-sandwich "piano-stool" complexes. All the Ru(II) complexes were characterized by analytical and spectral (UV-visible, FT-IR, 1 H NMR and 13 C NMR) studies. The molecular structure of the ligands (L2 and L4) and the complexes (2, 4 and 5) was confirmed by single crystal XRD. All the complexes were successfully screened as catalysts for the asymmetric transfer hydrogenation (ATH) of ketones using 2-propanol as the hydrogen source in the presence KOH. The ATH reactions proceeded with excellent yields (up to 99%) and very good enantioselectivity (up to 99% ee). The scope of the present catalytic system was extended to substituted aromatic ketones and few hetero aromatic ketones. Density functional theory (DFT) calculations predicted non-classical, concerted transition states for the ATH reactions. The catalytic activity of Ru-benzene complexes toward asymmetric reduction of ketones was significantly higher compared to analogues p-cymene complexes. Such enhanced efficiency and the product selectivity for Ru-benzene complexes compared to Ru-p-cymene complexes were rationalized by the computational study.Electronic supplementary information (ESI) available: A table of the X-ray crystallographic data, atomic coordinates in CIF format, the molecular structure of ligands L2 & L4, 1 H NMR and 13 C NMR spectra of all the ligands and complexes, GC and HPLC data are included. Cartesian coordinates, energies, and vibrational frequencies for all the reported structures, and optimized geometries and activation free energies for high energy TSs.

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Section: Asymmetric Transfer Hydrogenation Of Ketonescontrasting

confidence: 60%

Section: Synthesis Of Ru(ii)-benzene Complexesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Half-sandwich Ru(η⁶-C₆H₆) complexes with chiral aroylthioureas for enhanced asymmetric transfer hydrogenation of ketones – experimental and theoretical studies

Sheeba

Preethi

Nijamudheen

et al. 2015

Catal. Sci. Technol.

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“…[264] An X-ray diffraction study of the Ag(I) complex of the 1-(benzoyl)-3,3-(dibutyl) thiourea provided evidence that both chelate and monodentate coordination modes of complexation to silver(I) are present. Hence, each silver atom is coordinated to sulfur and oxygen atoms from one ligand in the (O,S) anionic mode and to bridging sulfur from another thiourea ligand.…”

Section: Metal Complexesmentioning

confidence: 99%

A review on the chemistry, coordination, structure and biological properties of 1-(acyl/aroyl)-3-(substituted) thioureas

Saeed

Flörke

Erben

2013

Journal of Sulfur Chemistry

198

123

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This review provides an overview of the chemistry, structure and potential applications of 1-(acyl/aroyl)-3-(mono-substituted) and 1-(acyl/aroyl)-3,3-(di-substituted) thioureas, with general formula R 1 C(O)N (1) HC(S)N (3) R 2 R 3 . In recent years, the title compounds have found extensive applications as ligands in coordination chemistry. The effect that nitrogen substituents exert on the intra-and intermolecular hydrogen-bonding interactions is discussed, including their role on the coordination properties displayed by these ligands. Novel applications of transition metal complexes bearing 1-(acyl/aroyl)-3-(mono-and di-substituted) thioureas are introduced. Biological aspects are also highlighted. As recently demonstrated, high-throughput screening assay and structure-activity analyses are feasible for this class of compounds. The chemical versatility of 1-(acyl)-3-(substituted) thiourea molecules and the derived metal complexes, together with the possibility of determining detailed structural properties, join biological applications in a promising interdisciplinary approach. The bibliography includes 382 references with emphasis on the literature appearing after 2007.

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Oxidorhenium(V) Complexes with Benzoylselenoureas

et al. 2014

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Oxidorhenium(V) complexes with N,N‐dialkyl‐N′‐benzoylselenoureas (HL) were prepared from reactions with (NBu4)[ReOCl4]. The formation of compounds such as [ReO(L‐κO,Se)2(OMe)] or [{ReO(L‐κO,Se)2}2O] suggests parallels with the established chemistry of corresponding benzoylthioureas, while the isolation of unusual species such as [ReO(L‐κO,Se)2(L‐κSe)], [{ReO(L‐κO,Se)2}2Se3] and the formation of the respective diselenide suggest a more complicated reaction pathway with the unstable selenium compounds, and one in which degradation products of the ligands also plays a role.

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Hypodentate coordination of N,N-di(alkyl/aryl)-N′-acylthiourea derivatives in Cu(I) complexes

Cited by 29 publications

References 35 publications

Half-sandwich Ru(η⁶-C₆H₆) complexes with chiral aroylthioureas for enhanced asymmetric transfer hydrogenation of ketones – experimental and theoretical studies

Half-sandwich Ru(η⁶-C₆H₆) complexes with chiral aroylthioureas for enhanced asymmetric transfer hydrogenation of ketones – experimental and theoretical studies

A review on the chemistry, coordination, structure and biological properties of 1-(acyl/aroyl)-3-(substituted) thioureas

Oxidorhenium(V) Complexes with Benzoylselenoureas

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Hypodentate coordination of N,N-di(alkyl/aryl)-N′-acylthiourea derivatives in Cu(I) complexes

Cited by 29 publications

References 35 publications

Half-sandwich Ru(η6-C6H6) complexes with chiral aroylthioureas for enhanced asymmetric transfer hydrogenation of ketones – experimental and theoretical studies

Half-sandwich Ru(η6-C6H6) complexes with chiral aroylthioureas for enhanced asymmetric transfer hydrogenation of ketones – experimental and theoretical studies

A review on the chemistry, coordination, structure and biological properties of 1-(acyl/aroyl)-3-(substituted) thioureas

Oxidorhenium(V) Complexes with Benzoylselenoureas

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Product

Resources

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Half-sandwich Ru(η⁶-C₆H₆) complexes with chiral aroylthioureas for enhanced asymmetric transfer hydrogenation of ketones – experimental and theoretical studies

Half-sandwich Ru(η⁶-C₆H₆) complexes with chiral aroylthioureas for enhanced asymmetric transfer hydrogenation of ketones – experimental and theoretical studies