Asymmetric transfer hydrogenation of acetophenone derivatives with novel chiral phosphinite based η6-p-cymene/ruthenium(II) catalysts

Aydemir, Murat; Meri̇ç, Nermin; Baysal, Akın; Turgut, Yılmaz; Kayan, Cezmi; Şeker, Sevil; Toğrul, Mahmut; Gümgüm, Bahattin

doi:10.1016/j.jorganchem.2010.12.027

Cited by 20 publications

(13 citation statements)

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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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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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“…A binuclear ruthenium complex 73 with P-donor ligand also gave good conversions and moderate to good enantioselectivities (up to 85% ee) when it was used as catalyst in the TH of aromatic ketones. 347 The ferrocene moiety has been extensively explored as a backbone of phosphine ligands in asymmetric synthesis, because of its relative air stability, easy modifiability, highly electron-donating property, and unique structure. Recently, some ferrocene-derived phosphine ligands have been utilized in transition-metal-catalyzed TH reactions, 348 in particular for ruthenium arene catalysts.…”

Section: Recent Advances and Trendsmentioning

confidence: 99%

The Golden Age of Transfer Hydrogenation

2015

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“…Thus, ligands 34, 39 35 40 and 36 41 show a very variable efficiency in the mentioned reaction. Not having a diamine-derived structure are the ligands 37 42 and 38, 43 which were reported to be in general efficient for the ATH of different phenones with BRu or CRu, respectively, in the presence of isopropanol and sodium hydroxide as the base.…”

Section: Phosphorous Containing Ligandsmentioning

confidence: 99%

Catalytic asymmetric transfer hydrogenation of ketones: recent advances

Foubelo

Nájera

Yus

2015

Tetrahedron: Asymmetry

201

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Abstract-In this review article we will consider the main processes on asymmetric transfer hydrogenation (ATH) of ketones from 2008 up today. The most effective organometallic compounds (derived from Ru, Rh, Ir, Fe, Os, Ni, Co, and Re) and chiral ligands (derived from amino alcohols, diamines, sulphur-and phosphorous-containing compounds, as well as heterocyclic systems) will be shown paying special attention to functionalized substrates, tandem reactions, processes under nonconventional conditions, supported catalysts, dynamic kinetic resolutions (DKR), the use of water as a green solvent, theoretical and experimental studies on reaction mechanisms, enzymatic processes and finally applications to the total synthesis of biologically active organic molecules. _____________________________________________________________________________________

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Asymmetric transfer hydrogenation of acetophenone derivatives with novel chiral phosphinite based η6-p-cymene/ruthenium(II) catalysts

Cited by 20 publications

References 52 publications

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

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

The Golden Age of Transfer Hydrogenation

Catalytic asymmetric transfer hydrogenation of ketones: recent advances

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Asymmetric transfer hydrogenation of acetophenone derivatives with novel chiral phosphinite based η6-p-cymene/ruthenium(II) catalysts

Cited by 20 publications

References 52 publications

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

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

The Golden Age of Transfer Hydrogenation

Catalytic asymmetric transfer hydrogenation of ketones: recent advances

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Product

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About

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

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