Method for synthesizing thioether compound

A thioether compound and compound technology, applied in the field of thioether compound synthesis, can solve the problems of not easy to obtain reducing agent, low pH value of the reaction system, poor chemoselectivity, etc., to overcome the difficulty of passing through the rare earth catalytic cycle, and to obtain simple , High atomic economy

Pending Publication Date: 2022-01-04
WENZHOU MEDICAL UNIV
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Problems solved by technology

However, such methods exist such as reducing agents are not easy to obtain [such as: (NH 4)4 Mo 2 Cl:NH 4 ClH 2 O], chemoselectivity is bad (as: diisobutyl aluminum hydride), the pH value of reaction system is lower (as: the reductive halogenation system of hydrogen halide), the shortcomings such as higher reaction temp

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  • Method for synthesizing thioether compound
  • Method for synthesizing thioether compound
  • Method for synthesizing thioether compound

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0027] Example 1

[0028] Preparation of diphenyl sulfide, the following structural formula:

[0029]

[0030] Under nitrogen, was added diphenyl sulfoxide starting material (0.3 mmol) and phenyl silane (0.9 mmol), catalyst Y [N (SiMe 3 ) 2 ] 3 (0.03mmol), 120 ℃ reaction 24h, 85% yield of product was isolated.

[0031] The separated product was purified by NMR, and the results are as follows:

[0032] 1 H NMR (CDCL 3 , 500MHz, ppm): δ7.35 (d, J = 7.5Hz, 4H), 7.31 (t, J = 7.5Hz, 4H), 7.25 (t, J = 7.5Hz, 2H).

[0033] 13 C NMR (CDCL 3 , 125MHz, ppm): δ135.93,131.19,129.33,127.18.

Example Embodiment

[0034] Example 2

[0035] 4,4'-xylene sulfide prepared following structural formula:

[0036]

[0037] Under nitrogen was added 4,4'-xylene feed sulfoxide (0.3 mmol) and phenyl silane (0.9 mmol), catalyst Y [N (SiMe 3 ) 2 ] 3 (0.03mmol), for 24h at 120 ℃, product was isolated in 84% yield.

[0038] The separated product was purified by NMR, and the results are as follows:

[0039] 1 H NMR (CDCl3,500MHz, ppm): δ7.25 (d, J = 8.2Hz, 4H), 7.11 (d, J = 8.2Hz, 4H), 2.33 (s, 6H). 13 C NMR (CDCl3,125MHz, ppm) δ137.00,132.78,131.18,130.03,21.20.

Example Embodiment

[0040] Example 3

[0041] Preparation of 4,4'-dichlorodiphenyl sulfide, the following structural formula:

[0042]

[0043] Under nitrogen was added 4,4'-dichlorodiphenyl sulfoxide starting material (0.3 mmol) and phenyl silane (0.9 mmol), catalyst Y [N (SiMe 3 ) 2 ] 3 (0.03mmol), for 48h at 120 ℃, product was isolated in 90% yield.

[0044] The separated product was purified by NMR, and the results are as follows:

[0045] 1 H NMR (CDCL 3 , 400MHz, ppm): δ7.27-7.29 (m, 4H), 7.24-7.26 (m, 4H). 13 C NMR (CDCL 3 , 125MHz, ppm): δ134.08,133.62,132.45,129.64.

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Abstract

The invention discloses a method for synthesizing a thioether compound, and belongs to the technical field of organic matter synthesis. The synthesis of the thioether compound with diversified structures is realized by catalyzing the deoxidation reduction of sulfoxide through rare earth, and particularly, the thioether compound is prepared by taking various sulfoxide compounds as raw materials and phenylsilane as a reducing agent under a rare earth catalysis system. The method is wide in raw material source or easy to prepare, simple and convenient to operate, controllable in selectivity, high in yield, mild in condition, free of organic solvent and wide in universality.

Description

technical field [0001] The invention relates to the technical field of synthesis of thioether compounds, in particular to a method for synthesizing thioether compounds. Background technique [0002] Thioether compounds are an important class of organic compounds and intermediates in organic synthesis. They are not only important components of natural products and medicines, but also have unique optical properties. It occupies a very important position in organic synthesis. Therefore, the development of diverse and efficient new methods for the synthesis of thioether compounds has always been an important topic in organic synthetic chemistry. [0003] Traditional methods for the reduction of sulfoxides to sulfides in the preparation of thioether compounds involve the use of low-valent metal species such as metal hydride reagents, halide ions, phosphorus compounds, Woollin's reagent, and phosphines. However, such methods exist such as reducing agents are not easy to obtain [...

Claims

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Application Information

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IPC IPC(8): C07C319/14C07C321/30C07C323/09C07C321/20B01J31/22
CPCC07C319/14B01J31/1805B01J2231/64C07C321/30C07C323/09C07C321/20
Inventor 郑理洲章芳俊张晨璐
Owner WENZHOU MEDICAL UNIV
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