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Preparation method of 1,3-disubstituted-3-aryl propylene compound and application thereof

A technology for aryl propylene and compounds, which is applied in the field of preparation and application of 1,3-disubstituted-3-aryl propylene compounds, can solve the problems of lack of high efficiency and high selectivity, and achieve easy conversion, derivatization, and application Broad, Accessible Effects

Active Publication Date: 2012-05-02
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is still a lack of efficient, highly selective, and environmentally friendly allyl-aryl coupling reactions

Method used

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  • Preparation method of 1,3-disubstituted-3-aryl propylene compound and application thereof
  • Preparation method of 1,3-disubstituted-3-aryl propylene compound and application thereof
  • Preparation method of 1,3-disubstituted-3-aryl propylene compound and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1: allyl carbonate compound and phenylboronic acid in Pd (OAc) 2 Allyl-aryl coupling reaction catalyzed by complex ligands and solvents

[0026] The allyl-aryl coupling reaction formula is as follows:

[0027]

[0028] Among them: mol is mole, ligand is ligand, solvent is solvent, Boc is tert-butoxycarbonyl, 2 mol% is used for bisphosphine ligand, and 4 mol% is used for monophosphine ligand.

[0029] As shown in Table 1, the allyl carbonate compounds and phenylboronic acid in Pd(OAc) 2 Allyl-aryl coupling reaction catalyzed by the complex ligand and organic solvent, and the corresponding yield:

[0030] Table 1

[0031]

[0032] Wherein, THF is tetrahydrofuran, and Toluene is toluene

[0033]

[0034] Of course, in this embodiment, the organic solvent can also be dioxane, methylene chloride, chloroform, benzene, ether, methanol, ethanol, isopropanol, n-butanol, tert-butanol, dimethyl Formamide or acetonitrile, etc., which can be realized by ...

Embodiment 2

[0035] Embodiment 2: Allyl carbonate compound 1a and phenylboronic acid (2a) in Pd(OAc) 2 Allyl-aryl coupling reaction catalyzed by the complex

[0036] As shown in Table 2, the allyl carbonate compound 1a and phenylboronic acid (2a) in Pd(OAc) 2 Allyl-aryl coupling reaction under the catalysis of the complex, the distribution ratio of ligands and solvent components, and the corresponding yields, wherein: the reaction solvent is tetrahydrofuran, the reaction temperature is 50 ° C, and the reaction time is 24 hours (where The reaction time of No. 7 is 48 hours).

[0037] Table 2

[0038]

Embodiment 3

[0039] Embodiment 3: Allyl carbonate compound 1a and phenylboronic acid (2a) in Pd (OAc) 2 The reaction temperature and time of the allyl-aryl coupling reaction catalyzed by the complex

[0040] As shown in Table 3, the allyl carbonate compound 1a and phenylboronic acid (2a) in Pd(OAc) 2 The reaction time, temperature and corresponding yield of the allyl-aryl coupling reaction catalyzed by the complex, where: 1a, 2a, Pd(OAc) 2 、PPh 3 The molar ratio with water is: 1:1.5:0.02:0.04:5; the reaction solvent is tetrahydrofuran.

[0041] table 3

[0042]

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Abstract

The invention discloses a preparation method of a 1,3-disubstituted-3-aryl propylene compound and an application thereof. A palladium complex, which is generated by coordination between Pd(OAc)2 and a ligand, is used as a catalyst, and an allyl carbonic ester compound reacts with an aryl boric acid compound to prepare the 1,3-disubstituted-3-aryl propylene compound. The palladium catalyst used in the method is easy to obtain; the reaction condition is mild; a chiral substrate can be utilized to obtain a configuration-reversed chiral product and the chiral conversion rate is high; and the obtained 1,3-disubstituted-3-aryl propylene compound is easy for conversion and derivatization, and can be used to prepare an aryl propionic acid anti-inflammatory and analgesic medicine.

Description

technical field [0001] The invention relates to a synthesis method and application of a compound in the technical field of chemical industry. Specifically, the reaction of allyl carbonate and aryl phenylboronic acid catalyzed by a metal palladium complex is used to synthesize 1,3-bis with high efficiency and high selectivity. The substituted-3-arylpropene compound also relates to the convenient synthesis of arylpropionic acid anti-inflammatory and analgesic drugs by simply oxidizing the 1,3-disubstituted-3-arylpropene compound. Background technique [0002] The Suzuki-Miyaura reaction is an important carbon-carbon bond formation reaction, and so far a variety of cross-coupling reactions between electrophiles and organoboronic acid compounds have been developed [(a) Fu, G. C. Acc. Chem. Res. 2008, 41 , 1555. (b) Martin, R.; Buchwald, S. L. Acc. Chem. Res. 2008, 41 , 1461. (c) Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58 , 9633. (d) Miyaura, N.; Suzuki, ...

Claims

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Application Information

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IPC IPC(8): C07C15/50C07C15/44C07C15/58C07C1/32C07C43/215C07C41/30C07C59/64C07C51/16C07C69/76C07C67/343C07C205/06C07C201/12C07D317/12
Inventor 张勇健李晨光邢菊香赵景明
Owner SHANGHAI JIAO TONG UNIV
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