Method for preparing (Z)-1,2-disulfide-1-olefin by catalysis of metal copper salt

A technology for catalytic preparation and metal copper salts, applied in chemical instruments and methods, formation/introduction of mercapto/thioether groups, preparation of thioethers, etc., to achieve the effects of diverse product structures, readily available raw materials, and simple preparation methods

Inactive Publication Date: 2013-12-25
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Nevertheless, in the preparation method of (Z)-1,2-disulfide-1-alkenes disclosed with practical value, so far, there is still no use of this simple and convenient method to prepare this type of important organic compound compound

Method used

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  • Method for preparing (Z)-1,2-disulfide-1-olefin by catalysis of metal copper salt
  • Method for preparing (Z)-1,2-disulfide-1-olefin by catalysis of metal copper salt
  • Method for preparing (Z)-1,2-disulfide-1-olefin by catalysis of metal copper salt

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024]

[0025] Under nitrogen protection, 171 mg of (Z)-1-bromo-2-p-methylphenylene sulfide-1-decene, Cs 2 CO 3 326mg, Cu 2 O 7mg, DMEDA 8μL, p-cresol 124mg, DMF 2mL, mix well, and react at 120°C for 24h. After the reaction was completed, it was cooled to room temperature, then 15 mL of water was added to the reactant, extracted with ethyl acetate, dried over anhydrous sodium sulfate, concentrated, and passed through a silica gel column (the volume ratio of petroleum ether to ethyl acetate was 50:1) to obtain The product (Z)-1,2-di-p-methylphenylene sulfide-1-decene, the obtained product was 157 mg, and the yield was 82%. 1 H NMR (400MHz, CDCl 3 ): δ7.32-7.27(m, 4H), 7.13-7.08(m, 4H), 6.45(s, 1H), 2.32(s, 3H), 2.31(s, 3H), 2.20(t, J=7.2 Hz, 2H), 1.49-1.46(m, 2H), 1.29-1.20(m, 10H), 0.87(t, J=6.8Hz, 3H); 13 C NMR (100MHz, CDCl 3): δ137.12, 137.11, 134.7, 132.8, 131.5, 130.4, 130.3, 130.1, 130.0, 128.8, 37.2, 32.1, 29.6, 29.5, 29.1, 28.8, 22.9, 21.4, 21.3, 14.4.

Embodiment 2

[0027]

[0028] Under nitrogen protection, 171 mg of (Z)-1-bromo-2-p-methylphenylene sulfide-1-decene, Cs 2 CO 3 326mg, Cu 2 O 7mg, TMEDA 15μL, p-cresol 124mg, DMF 2mL, react at 120°C for 24h. Cool to room temperature, add 15 mL of water, extract with ethyl acetate, dry over anhydrous sodium sulfate, concentrate, pass through a silica gel column (the volume ratio of petroleum ether to ethyl acetate is 50:1), and obtain the product (Z)-1,2 -Di-p-methylphenylene sulfide-1-decene, the product obtained was 148 mg, and the yield was 77%.

Embodiment 3

[0030]

[0031] Under nitrogen protection, 171 mg of (Z)-1-bromo-2-p-methylphenylene sulfide-1-decene, Cs 2 CO 3 326mg, Cu 2 O 7mg, DMEDA 8μL, p-cresol 124mg, THF 2mL, react at 120°C for 24h. Cool to room temperature, add 15 mL of water, extract with ethyl acetate, dry over anhydrous sodium sulfate, concentrate, pass through a silica gel column (the volume ratio of petroleum ether to ethyl acetate is 50:1), and obtain the product (Z)-1,2 -Di-p-methylphenylene sulfide-1-decene, the product obtained was 144 mg, and the yield was 75%.

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Abstract

The invention discloses a method for preparing (Z)-1,2-disulfide-1-olefin by the catalysis of metal copper salt, comprising the following steps of: using metal copper salt as a catalyst and using (Z)-1-bromine-2-thioether-1-olefin or mercaptan as a substrate under the action of alkaline in an organic solvent to synthesize (Z)-1,2-disulfide-1-olefin. The invention has the following advantages: the raw materials in the method are easily available; the preparation method is simple; as the catalyst, the metal copper salt is cheap and easily available; (Z)-1,2-disulfide-1-olefin prepared by the method has an extensive application prospect in the fields of coordination chemistry, material science, organic synthesis and the like.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for catalytically preparing (Z)-1,2-disulfide-1-alkene from metal copper salts. Background technique [0002] (Z)-1,2-disulfide-1-alkenes are a class of important organic compounds, which have broad application prospects in the fields of coordination chemistry, materials science and organic synthesis (Clemenson, P.I. in the literature The chemistry and solid state properties of nickel, palladium and platinum bis (maleonitriniledithiolate) compounds.Coord.Chem.Rev.1990, Kondo, T., etc. in the literature Metal-Catalyzed Carbon-Sulfur Bond Formation.Chem.Rev.2000 and Zyk, N.V., etc. It is reported in the literature Methods for the synthesis of vinyl sulfides.Russ.Chem.Rev.2003). [0003] There are two traditional methods for preparing this compound: 1) metal-catalyzed addition of disulfide compounds to alkynes; 2) addition reaction of thiol or thiophenol compounds to alkyn...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B45/06C07C319/14C07C321/28C07D333/34C07D213/70C07F15/00
Inventor 陈万芝徐辉夏钦钦
Owner ZHEJIANG UNIV
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