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A method for synthesizing allyl sulfide by direct functionalization of c-h bond

An allyl and sulfide technology, applied in chemical instruments and methods, physical/chemical process catalysts, organic chemistry, etc., to achieve the effect of fewer steps, mild reaction conditions, and high-efficiency synthesis

Active Publication Date: 2020-06-02
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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  • A method for synthesizing allyl sulfide by direct functionalization of c-h bond
  • A method for synthesizing allyl sulfide by direct functionalization of c-h bond
  • A method for synthesizing allyl sulfide by direct functionalization of c-h bond

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 1 2 reaction atmosphere Argon protection conditions air condition Yield 89％ 81％

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Abstract

The invention discloses a method for synthesizing allyl sulfide through direct functionalization of C-H bonds. The method is to add olefin compounds and thiol compounds with allyl C-H bonds in a system containing a photocatalyst and a solvent, and use visible light irradiation; the photocatalyst is a quantum dot / rod. In the present invention, under visible light irradiation, C-S bonds are directly constructed through direct functionalization of C-H bonds, thereby realizing the synthesis of allyl sulfide. The present invention uses quantum dots / rods as photocatalysts, has mild reaction conditions, does not require the participation of free radical initiators and oxidants, does not require pre-activation of the substrate, is simple to operate, and is atom-economical.

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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Patent Type & Authority Patents(China)
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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