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Transient metal complex compound, synthetic method and use thereof

A technology of transition metals and synthesis methods, applied in the field of new transition metal complexes and their synthesis, can solve problems such as difficult universality, and achieve the effect of simple synthesis methods

Inactive Publication Date: 2008-12-17
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, because it is difficult to realize the universality of catalysts for various ketone substrates, many chiral bisphosphine ligands have been designed and synthesized, and have achieved very good results in the asymmetric hydrogenation of ketones[Jing , W.; Hua, C.; Waihim, K.; Rongwei, G.; Zhongyuan, Z.; .; Jian, X.; Rongwei, G.; Chihung, Y.; Chan, S.C., Chem. Eur. J. 2003, 9, 2963], [Jian, H.X.; Xin, L.W.; F.Z.; Bao, M.F.; Hai, F.D.; Zhou, Q.L.J.Am.Chem.Soc.2003.125, 4404], [Mark, J.; William, H.; Daniela, H.; Christophe, M.; Lett.2000, 26, 4173]

Method used

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  • Transient metal complex compound, synthetic method and use thereof
  • Transient metal complex compound, synthetic method and use thereof
  • Transient metal complex compound, synthetic method and use thereof

Examples

Experimental program
Comparison scheme
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preparation example Construction

[0032] Catalyst preparation

[0033] Preparation method of the present invention can be further embodied as follows with the preparation process of representative compound:

[0034] method one

[0035] [The preparation of catalyst 8 is an example]

Embodiment 1

[0036] Example 1: Catalyst 8

[0037]

[0038] General method (method 1): under the protection of argon, 50mg (0.24mmol) RuCl 3 with 300mg (1.14mmol) PPh 3 Put it into a reaction tube and install a reflux device. Add 12 mL of anhydrous CH 3 OH, heated to reflux for 5 hours. At this time, a brownish-red solid precipitated, filtered under the protection of argon, washed the solid with anhydrous ether, dried the solvent under reduced pressure, and was directly used in the next reaction.

[0039] Under argon protection, put 153 mg (0.16 mmol) of the above powdered solid into a reaction tube, add 2 mL of anhydrous THF, add 140 μL of dry triethylamine and 26 mg (0.16 mmol) of dinitrogen ligand (S)-7, and stir at room temperature After reacting overnight, white insoluble matter precipitated out. Filtrate under Ar atmosphere, drain the filtrate to about 0.5 mL, add 6 mL of anhydrous diethyl ether, a brownish-yellow solid can be precipitated, filter under argon protection, th...

Embodiment 2

[0040] Example 2: Catalyst 9

[0041] Using Method 1, the yield: 76%.

[0042] 31 P NMR (121MHz, CDCl 3 ): δ 44.62 (d, J = 38.2 Hz), 42.80 (d, J = 38.2 Hz), 36.9 (d, J = 11.0 Hz) ppm.

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Abstract

The invention relates to a metal ruthenium complex with the general formula MXYLnL', other transition metal complexes, a synthetic method thereof and an application thereof. Dinitrogen ligand with active hydrogen reacts with transition metal under the action of alkali to generate a transition metal complex which has novel structure, contains phosphine and nitrogen and can be used for catalytic hydrogenation reaction with asymmetric transferring and also for the catalytic hydrogenation reaction, especially used for the catalytic asymmetric hydrogenation reaction of hypnone and derivatives, benzophenone and derivatives, Beta-N, N-dimethylamino-Alpha-hypnone and derivatives, and other ketone chemical compounds.

Description

technical field [0001] The invention relates to a novel transition metal complex and its synthesis method and application. The dinitrogen ligand with an active hydrogen reacts with the transition metal complex precursor under the action of a base to form a novel structure-containing phosphine-containing nitrogen-containing transition metal complex, which can be used for catalytic hydrogenation and transfer hydrogenation reactions, Especially for catalytic asymmetric hydrogenation of acetophenone and its derivatives, benzophenone and its derivatives, β-N,N-dimethylamino-α-acetophenone and its derivatives and other ketones reaction. Background technique [0002] Asymmetric catalytic hydrogenation is a hot spot in the current field of asymmetric synthesis, and has been increasingly used in industrial production [Ohkuma, T.; Kitamura, M.; Noryori, R. (1999) Asymmetric Hydrogenation.In: Ojiama , I. (ed) Catalytic Asymmetric Synthesis. (2nd Ed.). Wily-VCH: New York (Englinsh) 20...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C07F1/08C07F17/02C07B53/00C07B35/02C07C29/153
Inventor 克里斯蒂安·山多夫李跃辉
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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