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Preparation method of coupling aromatic compound

An aromatic compound and coupling technology, applied in the field of preparation of coupled aromatic compounds, can solve the problems of high toxicity, easy inactivation, limited industrial application, etc., and achieve the effects of mild reaction conditions and reduced use.

Active Publication Date: 2014-06-11
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to some defects of the phosphorus ligand itself, such as easy inactivation when encountering water and oxygen, and high toxicity, etc., its industrial application is greatly limited.

Method used

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  • Preparation method of coupling aromatic compound
  • Preparation method of coupling aromatic compound
  • Preparation method of coupling aromatic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The preparation of embodiment 1 oxime ether cyclopalladium complex

[0033] Add p-hydroxyacetophenone oxime (1.43g, 9.5mmol), lithium tetrachloropalladate (2.62g, 10.0mmol), sodium acetate (0.82g, 10.0mmol) and 8mL methanol, magnetic Stirring was heated and refluxed for 72 hours, the filter cake was removed by filtration, and 10 mL of distilled water was slowly added dropwise to the filtrate to obtain 2.16 g of a yellow-green solid with a yield of 75%.

[0034]

Embodiment 2

[0036] Add benzothiazole (135.2mg, 1.0mmol), iodobenzene (306.0mg, 1.5mmol) to the two-necked reaction flask, the oxime ether cyclopalladium complex (14.7mg, 0.05mmol) prepared by the method in Example 1, K 2 CO 3 (276.0mg, 1.5mmol), DMAc (5mL), under argon atmosphere, heated to 140 ° C, refluxed for 24 hours, after the reaction, the reaction solution was distilled off the solvent under reduced pressure, and the concentrate (residue) was subjected to silica gel column chromatography Separation [ethyl acetate and petroleum ether (volume ratio: 1:50) as the eluent], the eluate was collected at Rf value = 0.32, rotary evaporated, and dried to obtain 2-phenylbenzothiazole (I-1) 169.0 mg, yield 80%, white solid, melting point: 86-87°C.

[0037]

Embodiment 3～18

[0039] The reaction conditions are as shown in Table 1, and other operations are the same as in Example 2.

[0040] Table 1 Screening of reaction conditions

[0041]

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Abstract

The invention discloses a preparation method of a coupling aromatic compound, which comprises the following steps of taking non-functional aromatic hydrocarbon and / or halogenated aromatic hydrocarbon as a raw material, taking an oxime ether cyclopalladated complex as a catalyst, reacting for 6-48 hours in an organic solvent at a temperature of 100-160 DEG C under the inert atmosphere under the action of alkali, and post-processing reaction liquid after the end of reaction to obtain the coupling aromatic compound. The oxime ether cyclopalladated complex is a complex formed by reacting metal palladium salt with an organic nitrogen ligand in a methanol solvent at a room temperature; and the metal palladium salt is lithium tetrachloropalladate; and the organic nitrogen ligand is 4-hydroxy acetophenone oxime. The preparation method has the beneficial effects that when the oxime ether cyclopalladated complex is selected as the catalyst to replace a traditional palladium / phosphorus composite catalyst, the reaction condition can be milder and more efficient, so that the use of the ligand is greatly reduced; and the halogenated aromatic hydrocarbon which is lower in activity and cost and is easily obtained can also be used as a substrate in the reaction.

Description

(1) Technical field [0001] The invention relates to a method for preparing a coupling aromatic compound, in particular to a method for preparing a coupling aromatic compound by using an oxime ether cyclopalladium complex as a catalyst. (2) Background technology [0002] Coupled aromatic compounds are a class of compounds with important application value, which are widely used in the fields of synthetic drugs, liquid crystals and polymer materials [G.Bringmann, C.Gunther, M.Ochse, O.Schupp, S.Tasler, Progress in the Chemistry of Organic Natural Products, Vol82 (Eds.: W. Herz, H. Falk, G. W. Kirby, R. E. Moore), Springer, New York, 2001, pp 1-293.]. The main methods for the traditional construction of aromatic compounds include Suzuki [F.Alonso, I.P.Beletshaya, M.Yus, Tetrahedron 2008, 64, 3047-3101.], Kumada [J.-K.Huang, S.P.Nolan, J.Am.Chem. Soc.1999, 121, 9889-9890.], Stille [P.Espinet, A.M.Echavarren, Angew.Chem.Int.Ed.2004, 43, 4704-4730.] and other coupling reactions, t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B37/00C07D277/66C07D221/12
Inventor 张国富赵晓宝丁成荣严允兵
Owner ZHEJIANG UNIV OF TECH
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