Applications of N′-alkylated derivatives of TsDPEN in the asymmetric transfer hydrogenation of CO and CN bonds

Martins, José Eduardo Damas; Redondo, Miguel A. Contreras; Wills, Martin

doi:10.1016/j.tetasy.2010.07.013

Cited by 50 publications

(33 citation statements)

References 65 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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“…Indeed, piperidin-4-one derivative (S)-7 [16] was readily isolated in 83 % overall yield with 87 % ee when the reaction mixture was instead treated with Pd/C and acidic THF solvent under hydrogen atmosphere at room temperature for 6 h (Scheme 5). This shows that compound 1 is capable of serving as a methyl vinyl ketone (MVK) equivalent for (4+2) annulation with tosylimine (Scheme 5).…”

Section: Methodsmentioning

confidence: 99%

Amine‐Promoted Asymmetric (4+2) Annulations for the Enantioselective Synthesis of Tetrahydropyridines: A Traceless and Recoverable Auxiliary Strategy

Jiao

et al. 2013

Angewandte Chemie

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Spurlos verschwunden: 2‐(Acetoxymethyl)buta‐2,3‐dienoat reagiert in situ mit einem sekundären Amin zu einem 2‐Methylen‐3‐oxobutanoat‐Äquivalent, dessen asymmetrische [4+2]‐Ringschlüsse mit N‐Tosyliminen Tetrahydropyridine in guten bis ausgezeichneten Ausbeuten und Enantioselektivitäten liefern. Das Amin wirkt dabei als spurloses Auxiliar und kann leicht zurückgewonnen werden.

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“…21 More recently, several ansa-complexes have been developed for the same process, such as compounds 14-18, 22-25 which have been shown to be active in the ATH of ketones, mainly aromatic derivatives, using the formic acid/triethylamine combination as the hydrogen source giving variable yields and enantioselectivities.…”

Section: Diamines As Ligandsmentioning

confidence: 99%

Catalytic asymmetric transfer hydrogenation of ketones: recent advances

Foubelo

Nájera

Yus

2015

Tetrahedron: Asymmetry

199

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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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Applications of N′-alkylated derivatives of TsDPEN in the asymmetric transfer hydrogenation of CO and CN bonds

Cited by 50 publications

References 65 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

Amine‐Promoted Asymmetric (4+2) Annulations for the Enantioselective Synthesis of Tetrahydropyridines: A Traceless and Recoverable Auxiliary Strategy

Catalytic asymmetric transfer hydrogenation of ketones: recent advances

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Applications of N′-alkylated derivatives of TsDPEN in the asymmetric transfer hydrogenation of CO and CN bonds

Cited by 50 publications

References 65 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

Amine‐Promoted Asymmetric (4+2) Annulations for the Enantioselective Synthesis of Tetrahydropyridines: A Traceless and Recoverable Auxiliary Strategy

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