Screening of C2-symmetric chiral phosphinites as ligands for ruthenium(II)-catalyzed asymmetric transfer hydrogenation of prochiral aromatic ketones

Elma, Duygu; Durap, Feyyaz; Aydemir, Murat; Baysal, Akın; Meri̇ç, Nermin; Ak, Bünyamin; Turgut, Yılmaz; Gümgüm, Bahattin

doi:10.1016/j.jorganchem.2013.01.012

Cited by 29 publications

(13 citation statements)

References 46 publications

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“…S1). It is well known that phosphinites are generally unstable in the solid state and decompose rapidly on exposure to air or moisture . In contrast, we observe that our phosphinite ligands are highly stable in the solid state and do not decompose in the open‐air atmosphere in two weeks.…”

Section: Resultscontrasting

confidence: 50%

“…It is suggested that phosphinite dissociation occurs and the observed high stereocontrol is attributed to the inherent properties of the peptide backbone in the ligand structure . Partly because of their straightforward synthesis from readily available chiral diols, C 2 ‐symmetric bis(phosphinite) ligands also retain a privileged position in asymmetric transfer hydrogenation of ketones …”

Section: Introductionmentioning

confidence: 99%

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Synthesis, characterization and first application of chiral C₂‐symmetric bis(phosphinite)–Pd(II) complexes as catalysts in asymmetric intermolecular Heck reactions

Karakaş

Durap

Aydemir

et al. 2015

Applied Organom Chemis

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A series of new chiral C 2 -symmetric bis(phosphinite) ligands and their palladium(II) complexes have been synthesized and for the first time used as catalysts in the palladium-catalysed asymmetric intermolecular Heck coupling reactions of 2,3-dihydrofuran with iodobenzene or aryl triflate. Under optimized conditions, products were obtained with high conversions and moderate to good enantioselectivities. The new C 2 -symmetric bis(phosphinite) ligands and their palladium(II) complexes were characterized using multinuclear NMR and Fourier transform infrared spectroscopies and elemental analysis.

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Section: Resultscontrasting

confidence: 50%

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and first application of chiral C₂‐symmetric bis(phosphinite)–Pd(II) complexes as catalysts in asymmetric intermolecular Heck reactions

Karakaş

Durap

Aydemir

et al. 2015

Applied Organom Chemis

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“…[59][60][61][62][63][64][65][66][67][68][69][70][71][72][73] We have also reported the catalytic activity of these complexes in the TH of some acetophenone derivatives with the use of 2propanol in the presence of base.…”

Section: Discussionmentioning

confidence: 99%

Synthesis and Characterization of Half‐Sandwich Ruthenium Complexes Containing Aromatic Sulfonamides Bearing Pyridinyl Rings: Catalysts for Transfer Hydrogenation of Acetophenone Derivatives

et al. 2013

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Keywords: Transfer hydrogenation / Sulfonamides / Ruthenium / N ligands benzenesulfonamides 1-6 were successfully synthesized by the reaction of 8-aminoquinoline and various benzenesulfonyl chlorides. Then, half-sandwich ruthenium complexes 7-12 were prepared from the reactions of 1-6 with [RuCl 2 (p-cymene)] 2 . The synthesized compounds were characterized by NMR and FTIR spectroscopy and elemental analysis, and compounds 8 and 9 were further ana- [a]3224 lyzed by X-ray diffraction. The complexes were screened for their efficiency as catalysts in the transfer hydrogenation of acetophenone derivatives to phenylethanols in the presence of KOH with 2-propanol (as hydrogen source) at 82°C, and they all showed good activity. Complexes 10 and 12 were the most active (turnover frequency values: 703 and 734 h -1 , respectively). same time, half-sandwich ruthenium(II) complexes containing thioamides, 2-(diphenylphosphanyl)aniline, ferrocenyl tosylamine-phosphane and pyridine-based chelating diamine ligands were also studied for the catalytic TH of ketones. [34][35][36][37] Also, remarkable studies have been carried out in the TH of acetophenone derivatives. [38][39][40][41][42][43][44][45][46][47][48][49][50][51][52] Herein, a series of half-sandwich Ru II complexes containing sulfonamide ligands were synthesized and characterized by various spectroscopic techniques. The synthesized complexes were used as catalysts for the TH of acetophenone derivatives. Results and Discussion SynthesesThe synthesis and reaction routes to the ligands and to their corresponding Ru II complexes are presented in Fig-Figure 1. Synthesis of the ligands together with their NMR numbering scheme. Eur. J. Inorg. Chem. 2013, 3224-3232 Eur. J. Inorg. Chem. 2013, 3224-3232 {[N-Quinoline-8-yl-4-(trifluoromethyl)benzenesulfonamido](p-cymene)chlororuthenium(II)} (12): Yield 83 %, dark red microcrystals, m.p. 245-247°C. 1 H NMR (CDCl 3 ): δ = 0.94 and 1.09 (d and d,

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“…Catalytic reduction of unsaturated compounds via transfer hydrogenation is one of the most reliable methods of obtaining the corresponding saturated products which are versatile synthetic precursors that yield further functionalised molecules. As catalysts for the transfer hydrogenation of ketones, Ru(II) complexes bearing N, O or P donor ligands have all been used and are known to be effective catalysts . Transition metal complexes containing nitrogenous ligands phenanthroline and bipyridine are known to catalyse the reduction of ketones and imines using 2‐propanol as hydrogen source in basic medium .…”

Section: Introductionmentioning

confidence: 99%

Transfer hydrogenation of aryl ketones with homogeneous ruthenium catalysts containing diazafluorene ligands

Baran

Durap

Aydemir

et al. 2016

Applied Organom Chemis

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Novel cationic ruthenium(II) complexes bearing a 4,5‐diazafluorene unit and p‐cymene as ligands have been synthesised. The complexes were characterised based on elemental analysis and Fourier transform infrared and nuclear magnetic resonance spectroscopies. The synthesised Ru(II) complexes were employed as pre‐catalysts for the transfer hydrogenation of aromatic ketones using 2‐propanol as both hydrogen source and solvent in the presence of NaOH. All complexes showed high catalytic activity as catalysts in the reduction of substituted acetophenones to corresponding secondary alcohols. The products of catalysis were obtained with conversion rates of between 80 and 99%. Among the seven new complexes investigated, the most efficient catalyst showed turnover frequencies in the range 255–291 h−1 corresponding to 85 to 97% conversion, respectively. Copyright © 2016 John Wiley & Sons, Ltd.

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Screening of C2-symmetric chiral phosphinites as ligands for ruthenium(II)-catalyzed asymmetric transfer hydrogenation of prochiral aromatic ketones

Cited by 29 publications

References 46 publications

Synthesis, characterization and first application of chiral C₂‐symmetric bis(phosphinite)–Pd(II) complexes as catalysts in asymmetric intermolecular Heck reactions

Synthesis, characterization and first application of chiral C₂‐symmetric bis(phosphinite)–Pd(II) complexes as catalysts in asymmetric intermolecular Heck reactions

Synthesis and Characterization of Half‐Sandwich Ruthenium Complexes Containing Aromatic Sulfonamides Bearing Pyridinyl Rings: Catalysts for Transfer Hydrogenation of Acetophenone Derivatives

Transfer hydrogenation of aryl ketones with homogeneous ruthenium catalysts containing diazafluorene ligands

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Screening of C2-symmetric chiral phosphinites as ligands for ruthenium(II)-catalyzed asymmetric transfer hydrogenation of prochiral aromatic ketones

Cited by 29 publications

References 46 publications

Synthesis, characterization and first application of chiral C2‐symmetric bis(phosphinite)–Pd(II) complexes as catalysts in asymmetric intermolecular Heck reactions

Synthesis, characterization and first application of chiral C2‐symmetric bis(phosphinite)–Pd(II) complexes as catalysts in asymmetric intermolecular Heck reactions

Synthesis and Characterization of Half‐Sandwich Ruthenium Complexes Containing Aromatic Sulfonamides Bearing Pyr­id­inyl Rings: Catalysts for Transfer Hydrogenation of Acetophenone Derivatives

Transfer hydrogenation of aryl ketones with homogeneous ruthenium catalysts containing diazafluorene ligands

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Synthesis, characterization and first application of chiral C₂‐symmetric bis(phosphinite)–Pd(II) complexes as catalysts in asymmetric intermolecular Heck reactions

Synthesis, characterization and first application of chiral C₂‐symmetric bis(phosphinite)–Pd(II) complexes as catalysts in asymmetric intermolecular Heck reactions

Synthesis and Characterization of Half‐Sandwich Ruthenium Complexes Containing Aromatic Sulfonamides Bearing Pyridinyl Rings: Catalysts for Transfer Hydrogenation of Acetophenone Derivatives