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Method for synthesizing allyl sulfides by means of direct functionalization of C-H bonds

An allyl and sulfide technology, applied in chemical instruments and methods, physical/chemical process catalysts, sulfide preparation, etc., to achieve the effects of reducing reaction steps, reducing costs, and mild reaction conditions

Active Publication Date: 2018-07-20
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Therefore, as of now, there are no patents and literature reports on the synthesis of allyl sulfides through direct functionalization of C-H bonds.

Method used

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  • Method for synthesizing allyl sulfides by means of direct functionalization of C-H bonds
  • Method for synthesizing allyl sulfides by means of direct functionalization of C-H bonds
  • Method for synthesizing allyl sulfides by means of direct functionalization of C-H bonds

Examples

Experimental program
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Effect test

Embodiment 1

[0042] The synthesis of compound cyclohexyl-2-en-1-yl (4-methoxyphenyl) sulfane, the steps are as follows:

[0043] 1) Take 7mL concentration to be 8.0×10 -5 mol / L CdSe quantum dot aqueous solution, adding 0.1mL concentration is the mixed solution of nitric acid of 2mol / L, this mixed solution is centrifuged on the centrifuge, removes the upper layer aqueous solution, obtains solid substance; The purpose of this step is (1) to remove Ligands on the surface of quantum dots; (2) remove the solvent water by centrifugal precipitation to obtain solid matter, which is beneficial to use other solvents for research.

[0044] 2) Add the solid substance in step 1) to 4 mL of acetonitrile, and ultrasonicate for 2 minutes to obtain a clear mixed solution of acetonitrile;

[0045] 3) Add the mixed solution in step 2) to a 10mL test tube, and add 0.1mmol 4-methoxythiophenol and 5mmol cyclohexene to the acetonitrile mixed solution to obtain a reaction solution;

[0046] 4) Under the protect...

Embodiment 2

[0051] The effect of the reaction under the air condition and under the protection condition of argon was compared. The steps of the method are the same as in Example 1, except that the conditions in step 4) are changed, that is, under air conditions, the reaction solution in step 3) is irradiated with LED blue light for 20 h. The results are shown in Table 1:

[0052] Table 1 reacts effect comparison under air condition and argon protection condition

[0053] Example

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Abstract

The invention discloses a method for synthesizing allyl sulfides by means of direct functionalization of C-H bonds. According to the method, olefin compounds having allylic C-H bonds and thiol compounds are added to a system containing a photocatalyst and a solvent, and the system is irradiated with visible light; the photocatalyst is quantum dots / rods. C-S bonds are directly constructed by meansof direct functionalization of the C-H bonds under the irradiation of the visible light, so that the synthesis of the allyl sulfides is realized. The method uses the quantum dots / rods as the photocatalyst, so that the reaction conditions are mild; the participation of free radical initiators and oxidants is not needed, and a substrate does not need to be pre-activated, so that the method is simpleto operate and has atom economy.

Description

technical field [0001] The invention relates to the technical field of catalytic synthesis. More specifically, it relates to a method for the synthesis of allyl sulfides through direct functionalization of C-H bonds. Background technique [0002] Allyl sulfides are an important class of organic compounds, which are widely used in many fields such as organic synthetic chemistry, chemical biology and medicinal chemistry. Therefore, it is of great synthetic significance to establish a simple and efficient method for the synthesis of allyl sulfides. At present, the techniques for synthesizing allyl sulfides mainly include the rearrangement reaction of allyl compounds and the substitution reaction of allyl derivatives catalyzed by transition metals. For example, in 1986, Bosnich et al. synthesized allyl sulfides (Auburn, P.R; Whelan, J.; Bosnich, B.J. Chem. Soc., Chem. Commun .1986,2,146,Homogeneous catalysis.Production of allyl alkylsulphides by palladium mediated allylation)...

Claims

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Application Information

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IPC IPC(8): C07C319/14B01J27/057B01J27/04C07C321/28C07C323/09C07C323/20C07C323/35
CPCC07C319/14B01J27/04B01J27/057B01J35/39C07C321/28C07C323/09C07C323/20C07C323/35
Inventor 吴骊珠黄程佟振合
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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