Asymmetric transfer hydrogenation of ketones catalyzed by ruthenium(II) complexes bearing a chiral phosphinoferrocenyloxazoline ligand

Madrigal, Cesar A.; García‐Fernández, Almudena; Gimeno, José; Lastra, Elena

doi:10.1016/j.jorganchem.2008.04.027

Cited by 29 publications

(18 citation statements)

References 44 publications

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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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“…Asymmetric transfer hydrogenation (ATH) of ketones by organometallic homogeneous catalysis in water is of abundant attention in green chemistry. Recently, many have described the ATH of ketones in water solvent under non‐inert conditions, which are useful for industrial applications . Chiral Ru (II)‐ p ‐cymene complexes are found to be promising catalysts for ATH of ketones.…”

Section: Introductionmentioning

confidence: 99%

Water soluble Ru (II)–p‐cymene complexes of chiral aroylthiourea ligands derived from unprotected D/L‐alanine as proficient catalysts for asymmetric transfer hydrogenation of ketones

Sheeba

Tamizh

Bhuvanesh

et al. 2018

Applied Organom Chemis

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The newfangled chiral aroylthiourea ligands (L1‐L6) were produced from unprotected D/L‐alanine and their water soluble Ru (II) organometallic catalysts (1–6) were designed from their reaction with [RuCl2(η6‐p‐cymene)]2. The analytical and spectral methods were used to confirm the structure of the ligands and complexes. The solid state structure of L1, 5 and 6 was confirmed by single crystal XRD. The organometallic compounds (1–6) catalyzed the asymmetric transfer hydrogenation of aromatic, heteroaromatic and bulky ketones to yield respective enantiopure secondary alcohols with admirable conversions (up to 99%) and attractive enantiomeric excesses (ee up to 98%), in presence of formic acid and triethylamine in water medium under non‐inert atmospheric conditions.

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“…44 Two phosphine derivatives, namely compounds 40 45 and 41 46 were reported to be active in combination with the ruthenium dichloride-triphenyl phosphine complex for the ATH of phenones in the presence of isopropanol and sodium hydroxide as base. Actually, the corresponding isolated complexes were directly used in the reaction.…”

Section: Phosphorous Containing Ligandsmentioning

confidence: 99%

Catalytic asymmetric transfer hydrogenation of ketones: recent advances

Foubelo

Nájera

Yus

2015

Tetrahedron: Asymmetry

214

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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 ketones catalyzed by ruthenium(II) complexes bearing a chiral phosphinoferrocenyloxazoline ligand

Cited by 29 publications

References 44 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

Water soluble Ru (II)–p‐cymene complexes of chiral aroylthiourea ligands derived from unprotected D/L‐alanine as proficient catalysts for asymmetric transfer hydrogenation of ketones

Catalytic asymmetric transfer hydrogenation of ketones: recent advances

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Asymmetric transfer hydrogenation of ketones catalyzed by ruthenium(II) complexes bearing a chiral phosphinoferrocenyloxazoline ligand

Cited by 29 publications

References 44 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

Water soluble Ru (II)–p‐cymene complexes of chiral aroylthiourea ligands derived from unprotected D/L‐alanine as proficient catalysts for asymmetric transfer hydrogenation of ketones

Catalytic asymmetric transfer hydrogenation of ketones: recent advances

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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