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Catalyst for catalyzing thioether oxidation as well as preparation method and application of catalyst

A catalyst and oxidant technology, used in the preparation of organic compounds, physical/chemical process catalysts, organic compound/hydride/coordination complex catalysts, etc., can solve problems such as inapplicability, and achieve mild conditions, good selectivity, The effect of high product purity

Inactive Publication Date: 2015-05-06
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

It is also possible to synthesize sulfone through Suzuki coupling reaction. For example, Chinese patent (CN 103922976 A) uses aryl sulfinate and aryl fluoroborate to synthesize diaryl sulfone through Suzuki coupling reaction under the catalysis of CuCl to obtain the product Asymmetric diaryl sulfone products with a yield greater than 90%, but this method is only suitable for the synthesis of diaryl sulfones, not suitable for sulfones containing alkyls

Method used

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  • Catalyst for catalyzing thioether oxidation as well as preparation method and application of catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Example 1. Synthesis of Salen Ligand

[0020] Into a 250 mL three-necked flask, 2.56 g of the compound, 10.0 mmol of 5-bromo-3-tert-butyl salicylaldehyde, 0.29 g, 4.9 mmol of ethylenediamine (the molar ratio of the two was 1:0.49) and 150 mL of ethanol were added successively. After reacting for 12 h at 85 °C under the protection of an inert gas, it was cooled to 15 °C, and the reaction solution was evaporated at 40 °C by a rotary evaporator, concentrated to 10 mL, and then placed at -5 °C for 3 h. Suction filtration with a Buchner funnel, the filter cake was washed with 10 mL ice ethanol for 3 to 5 times, and the filter cake was collected to obtain 2.50 g of light yellow solid, 4.67 mmol Salen ligand, yield: 95%. 1 H NMR (CD 3 Cl, 400MHz) δ(ppm): 1.43[s, 18H, C(CH 3 ) 3 ], 3.97(s, CH 2 , 4 H), 7.23(s, Ar-H, 2 H), 7.38(s, Ar-H, 2 H), 8.32(s, N=CH, 2 H), 13.84 (s, 1 H, OH) .

Embodiment 2

[0021] Example 2. Synthesis of Ni(Ⅲ)Salen-OAc Catalyst

[0022] Into a 250 mL three-necked flask, 2.00 g, 3.73 mmol of Salen ligand, 1.1 g, 4.48 mmol of Ni(OAc) 2 · 4H 2 O, 60 mL of ethanol and 60 mL of chloroform were reacted at 80 °C for 12 h under the protection of inert gas nitrogen, and reacted with oxygen for 16 h. After the reaction, the solvent was recovered by rotary evaporation at 50 °C, washed twice with water, and reduced Suction filtration and air-drying at room temperature for 5 h gave 2.35 g, 3.61 mmol of Ni(Ⅲ) catalyst. Yield 97%; Elemental analysis (C 26 h 31 N 2 o 4 Br 2 Ni), theoretical values: C, 47.75 %; H, 4.78; N, 4.28 %; O, 9.78 %. Found: C, 47.78 %; H, 4.74 %; N, 4.25 %; O, 9.82 %. High-resolution mass spectrum: calculated value: 591.9865, experimental value: 591.9858.

Embodiment 3

[0023] Example 3. Synthesis of Mn(Ⅲ)Salen-OAc Catalyst

[0024] Into a 250 mL three-neck flask, 2.0 g, 3.73 mmol of Salen ligand, 1.3 g, 4.48 mmol of Mn(OAc) were sequentially added 2 · 6H 2 O, 60 mL of ethanol and 60 mL of chloroform were reacted at 80 °C for 12 h under the protection of inert gas nitrogen, and then reacted with oxygen for 16 h. filtered, and air-dried at room temperature for 5 h to obtain 2.35 g of Mn(Ⅲ) catalyst with a yield of 97%. Elemental analysis (C 26 h 31 N 2 o 4 Br 2 Mn), theoretical values: C,4 8.02 %; H, 4.80; N, 4.31 %; O, 9.84 %. Found: C, 47.78 %; H, 4.77 %; N, 4.28 %; O, 9.82 %. High-resolution mass spectrum: calculated value: 588.9893, experimental value: 588.9876.

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Abstract

The invention discloses a catalyst for catalyzing thioether oxidation as well as a preparation method and application of the catalyst. The preparation method comprises the following steps: synthesizing a bromated Salen ligand from bromosalicylaldehyde and ethanediamine by virtue of Schiff base condensation at first; and then adding a divalent metal salt to coordinate with the Salen ligand, and introducing oxygen for oxidation after complete reaction, thereby obtaining the catalyst for catalyzing thioether oxidation. The catalyst can be used for catalyzing the thioether oxidation of methyl phenyl sulfide, ethyl phenyl sulfide, n-butyl sulfide, dibenzyl sulfide and the like with relatively high activity and relatively high selectivity; and a sulfoxide product is generated when an axial ligand is added, and a sulfone product is generated when the axial ligand is not added.

Description

technical field [0001] The invention belongs to the technical field of catalysts, and specifically relates to an M (III) Salen catalyst, a preparation method thereof, and an application of the catalyst to controllably catalyze the oxidation of sulfide to generate sulfoxide and sulfone compounds. Background technique [0002] Sulfoxides and sulfones have a wide range of biological activities and have broad application prospects in medicine. As a chiral auxiliary, sulfoxide is often used in organic synthesis; as an oxidant, it can oxidize alcohols to aldehydes / ketones; in addition, activated sulfoxide plays an important role in the synthesis of oligosaccharides. Sulfone compounds are important intermediates in organic synthesis, and have shown excellent effects in medicine, insecticide, and weed control. The most direct and most commonly used synthesis of sulfoxide is the oxidation of sulfide, but sulfoxide is easily further oxidized into sulfone, which seriously affects the ...

Claims

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Application Information

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IPC IPC(8): B01J31/22C07C315/02C07C317/14C07C317/10C07C317/22C07C317/44
Inventor 白正帅鲍晓军范吉理
Owner FUZHOU UNIV
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