Method for synthesizing novel glutaric acid compound from bisaryl-substituted non-activated olefin

A technology for activating alkenes and glutaric acid, which is applied in the preparation of organic compounds, chemical instruments and methods, and the preparation of cyanide reactions. Wide application range and mild reaction conditions

Active Publication Date: 2021-09-28
SICHUAN UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the dicarboxylation of alkenes involving CO2 has been partially reported, the scope of substrates is mostly limited to activated alkenes.
So far, the method of constructing novel diacid compounds by using visible light-driven CO2 to participate in the dicarboxylation of non-activated alkenes has not been reported

Method used

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  • Method for synthesizing novel glutaric acid compound from bisaryl-substituted non-activated olefin
  • Method for synthesizing novel glutaric acid compound from bisaryl-substituted non-activated olefin
  • Method for synthesizing novel glutaric acid compound from bisaryl-substituted non-activated olefin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] This example provides a method for constructing novel glutaric acid compounds through the aryl migration strategy of non-activated olefin compounds substituted with different amino groups. The specific steps are as follows:

[0029] In a dried 10mL Schlenk tube (with stirring bar), accurately weigh different amino-substituted non-activated olefin compounds (0.2mmol, 1.0equiv), reducing agent triphenylsilane (104mg, 0.4mmol, 2.0equiv), The photosensitizer 3DPA2FBN (2.6mg, 2mol%) was added to the reaction tube, and then the reaction tube was moved to the glove box to add the base Cs 2 CO 3 (196 mg, 0.6 mmol, 3.0 equiv), after which the reaction tube was sealed using the corresponding stopcock of the reaction tube and removed from the glove box. Under the double-row gas guide system, the gas in the reaction tube is replaced by CO 2 Atmosphere, repeated 3 times; followed by CO 2 Add the hydrogen-absorbing reagent triisopropylsilylthiol (9μL, 0.04mmol, 20mol%) and the ult...

Embodiment 2

[0034] This example provides a method for constructing a novel glutaric acid compound from a non-activated olefin compound substituted with a symmetrical bisaryl group. The reaction steps are the same as those in Example 1, except that the reaction substrate is different, the specific structure and yield of the product And the ratio of diastereomers is shown in Table 2, and the specific reaction formula is shown in the following formula.

[0035]

[0036] Table 2 Corresponding products, yields and ratios of diastereomers of non-activated olefins substituted with different symmetrical bisaryl groups

[0037]

Embodiment 3

[0039] This example provides a method for constructing novel glutaric acid compounds from non-activated olefin compounds substituted by asymmetric bisaryl groups. The reaction steps are the same as those in Example 1, except that the reaction substrates are different. Ratio and diastereomer ratio are shown in Table 3, and the specific reaction formula is shown in the following formula.

[0040]

[0041] Table 3 Corresponding products, yields and ratios of diastereomers of different asymmetric bisaryl substituted non-activated alkenes

[0042]

[0043] The above experimental results show that non-activated alkene substrates with different amine substitutions, symmetrical aryl substitutions, and asymmetric aryl substitutions can all be synthesized with high yields and regioselectivities as well as moderate to good diastereoselectivities. A novel glutaric acid compound was obtained. Under this reaction system, substrates with different electrical properties can be compatib...

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Abstract

The invention discloses a method for synthesizing a novel glutaric acid compound from bisaryl-substituted non-activated olefin, belonging to the technical field of organic synthesis. The synthesis method comprises the following steps: adding a bisaryl-substituted non-activated olefin reaction substrate, a photosensitizer, a reducing agent and alkali into a reaction container, then adding a hydrogen abstraction reagent and a solvent in a CO2 atmosphere, conducting stirring at room temperature for 0.2-48 hours under a visible light irradiation condition, carrying out acidification quenching treatment on a reaction system after the reaction is completed, and carrying out separation and purification on a reaction product so as to prepare a novel glutaric acid product. The synthesis method disclosed by the invention has the characteristics of mild reaction conditions, high product yield, a wide substrate application range, relatively good functional group compatibility and the like; and the diacid product has potential application value, and the method is an environment-friendly and efficient strategy for synthesizing the diacid compound with a complex structure.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a method for constructing novel glutaric acid compounds through an aryl migration strategy driven by a bisaryl-substituted non-activated alkene substrate. Background technique [0002] The synthesis of highly functionalized diacids is of great significance in pharmaceuticals, organic synthesis, and polymer synthesis, especially as monomers for the synthesis of polyesters and polyamides, and has been widely used in industry on a large scale. For the preparation of diacids, the traditional method mainly uses nitric acid to selectively oxidize alcohols, cyclohexanol and cyclohexanone. However, the greenhouse gas nitrous oxide (N 2 The formation of O) violates the principles of green chemistry and is limited to the preparation of symmetrical diacids with this method. Although transition metal-catalyzed dicarbonylation of dienes or allyl alcohols is an alternati...

Claims

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Application Information

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IPC IPC(8): C07C227/02C07C229/36C07C231/12C07C233/47C07C233/51C07C233/87C07D307/68C07D333/24C07D333/38
CPCC07C227/02C07C231/12C07D333/38C07D307/68C07D333/24C07C229/36C07C233/51C07C233/47C07C233/87
Inventor 余达刚于博肖汉至李茜茜颜思顺鲍莹
Owner SICHUAN UNIV
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