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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 reaction The effect of mild conditions and high chiral conversion rate

Active Publication Date: 2014-06-18
SHANGHAI JIAOTONG 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

Examples

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., whic...

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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PUM

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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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Patent Type & Authority Patents(China)
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 JIAOTONG UNIV