Cage-shaped supramolecular catalyst for catalyzing thioether oxidation as well as preparation method and application of cage-shaped supramolecular catalyst

A technology for catalyzing sulfides and supramolecules, applied in the preparation of organic compounds, organic compound/hydride/coordination complex catalysts, physical/chemical process catalysts, etc., can solve the problems of poor stability and low activity of catalysts

Active Publication Date: 2021-05-11
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In order to overcome the problems in the existing technology, the present invention provides a new idea for the preparation and application of a caged supramolecular catalyst that catalyzes the oxidation of thioether. In this process, the conditions of the catalytic reaction syst

Method used

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  • Cage-shaped supramolecular catalyst for catalyzing thioether oxidation as well as preparation method and application of cage-shaped supramolecular catalyst
  • Cage-shaped supramolecular catalyst for catalyzing thioether oxidation as well as preparation method and application of cage-shaped supramolecular catalyst
  • Cage-shaped supramolecular catalyst for catalyzing thioether oxidation as well as preparation method and application of cage-shaped supramolecular catalyst

Examples

Experimental program
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Effect test

Embodiment 1

[0030] Example 1. Synthesis of covalent cage compound SNC containing Salen ligand

[0031] Weigh 122 mg of 2,4,6-triethyl-1,3,5-tris(4-oxomethyl-1-formyl)benzene c into a 50 mL round bottom flask, add 30 mL of trichloro After methane was completely dissolved, 45 μL of 1,2-cyclohexanediamine was added to the reaction system, and reacted at 60 °C for 12 h. After the reaction is complete, the reaction solution is distilled off under reduced pressure to remove the solvent, the filter cake is washed with acetonitrile, and the washed yellow solid powder is vacuum-dried to obtain the supramolecular cage compound SNC-2. 1 H NMR (400 MHz, CDCl3) δ 13.93(s, 6H), 8.34 – 8.10 (m, 6H), 7.12 (ddd, J = 20.9, 15.5, 8.8 Hz, 6H), 6.69 –6.35 (m, 12H), 3.94 – 3.19 (m, 12H), 2.92 – 2.58 (m, 12H), 1.35 – 1.10 (m, 18H).

Embodiment 2

[0032] Embodiment 2. The synthesis of caged supramolecular catalyst compound Ni(II)-SNC

[0033] Into a 250 mL three-neck flask, 290 mg SNC and 150 mg nickel acetate tetrahydrate were added sequentially, and 120 mL chloroform / ethanol (2:1, v: v) mixed solution was added under nitrogen atmosphere, and the reaction was refluxed at 80 °C for 12 h. After the reaction was complete, it was cooled to room temperature, concentrated to remove the solvent, washed with water and dried in vacuum to obtain Ni(II)-SNC. Infrared (FT-IR) spectrum results show at 535 cm -1 The characteristic absorption peak of Ni-N bond appears at 469 cm -1 The stretching vibration peak of the Ni-O bond appears. Electrospray-high resolution mass spectrometry (HR-MS, ESI): [C 90 h 96 N 6 o 12 Ni 3 +H + ] m / z, calculated value: 1629.50 m / z; experimental value: 1629.43 m / z.

Embodiment 3

[0034] Example 3. Catalyzed oxidation of sulfide anisole by caged supramolecular compound Ni(II)-SNC

[0035] Add 80 mg Ni(II)-SNC catalyst, 600 mg sulfide anisole, 210 mg 4-methylpyridine oxide, 60 mL methanol and 2.0 g iodobenzenediacetic acid to a 100 mL round-bottomed flask and react at 40 °C After 6 h, it was allowed to stand at room temperature, and the reaction solution was concentrated by rotary evaporation. Then, 0.666 g of benzoin was obtained by separation on a silica gel column with ethyl acetate / n-pentane as the eluent. Yield: 99.1%

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Abstract

The invention discloses preparation and application of a cage-shaped supramolecular catalyst for catalyzing thioether oxidation. The preparation method comprises the following steps: firstly, carrying out amine-aldehyde condensation on a tridentate aldehyde compound and 1, 2-cyclohexanediamine to obtain a covalent cage compound material containing a Salen ligand, then carrying out in-situ synthesis on the ligand and transition metal M (II) to obtain a target cage supramolecular catalyst material, and finally, applying the target cage supramolecular catalyst material to selective oxidation of thioether to generate sulfone or sulfoxide compounds. The catalyst material obtained by the method shows excellent performance in the catalytic thioether oxidation reaction, the conversion rate is up to 95% or above, the catalytic reaction condition involved in the technology is mild, the reaction solvent is greener, and the catalyst has the advantages of high conversion rate, high selectivity and the like, can be recycled for multiple times, the activity and the selectivity of the catalyst are not obviously reduced, and the catalyst has high economic benefits and industrial production application values.

Description

technical field [0001] The invention belongs to the technical field of catalysts, and in particular relates to a cage supramolecular catalyst for catalyzing thioether oxidation, a preparation method and application thereof. Background technique [0002] Sulfoxide (sulfone) compounds have a wide range of biological activities, and as bacteriostats, insecticides and antitumor drugs, they are also of great application value in the fields of pesticides and pharmaceuticals, as well as in the fields of fine chemistry such as food additives. The research progress of exploring new synthesis methods and the development of new catalysts has also been continuously reported, and the use of transition metal catalysis to synthesize sulfoxide is one of its important preparation methods. [0003] CN105879914B discloses a temperature-sensitive ionic liquid chiral Salen Ti complex catalyst and a preparation method thereof; the catalyst simultaneously includes a chiral Salen Ti complex catalys...

Claims

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Application Information

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IPC IPC(8): B01J31/22C07C315/02C07C317/14C07C317/10C07C317/04C07C317/18C08G83/00
CPCB01J31/2217C07C315/02C08G83/008B01J2531/847B01J2531/0252B01J2231/70C07C317/14C07C317/10C07C317/04C07C317/18Y02P20/584
Inventor 白正帅王梦美鲍晓军朱海波崔勍焱王廷海岳源源袁珮
Owner FUZHOU UNIV
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