Method for synthesizing trisubstituted arylphosphine oxide species by using diphenyl(tert-butyl)phosphine as substrate

A technology of diphenyl tertiary and aryl phosphine oxides, which is applied in chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, organic chemistry, etc., to reduce synthesis costs, avoid the use of precious metals, and achieve high yields Effect

Pending Publication Date: 2021-07-27
XINXIANG RUNYU NEW MATERIAL TECH CO LTD
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Problems solved by technology

[0004] The present invention provides a method for synthesizing trisubstituted aryl phosphine oxide species with diphenyl tert-butyl phosphine as a substrate, so as to solve the current problems in the synthesis of triaryl phosphine oxide compounds

Method used

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  • Method for synthesizing trisubstituted arylphosphine oxide species by using diphenyl(tert-butyl)phosphine as substrate
  • Method for synthesizing trisubstituted arylphosphine oxide species by using diphenyl(tert-butyl)phosphine as substrate
  • Method for synthesizing trisubstituted arylphosphine oxide species by using diphenyl(tert-butyl)phosphine as substrate

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Embodiment 1

[0020] In a 25mL Schlenk tube, put 0.2mmol (48mg) of diphenyl tert-butylphosphine, 0.6mmol (83mg) of p-methoxyphenylhydrazine, 2.3mg of palladium acetate (5mmol%), 0.6mmol of sodium carbonate (64mg) and 2mL of water, fill the Shrek tube with oxygen; heat up to 100°C with stirring, stop the reaction after 24 hours, cool to room temperature and extract the organic matter with dichloromethane, spin the dichloromethane extract to dryness and pass through column chromatography 46 mg of white solid was isolated. The structure of the product was determined to be (4-methoxyphenyl)diphenylphosphine oxide by NMR, and the yield was 75%.

[0021] Different hydrazine compounds, palladium salt catalysts and different reaction conditions were selected, and trisubstituted arylphosphine oxide species were synthesized by the same method as in Example 1. The reaction results are shown in Table 1.

[0022] Table 1 Catalyzed synthesis of three substituted arylphosphine oxide species reaction resu...

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Abstract

The invention relates to a method for synthesizing a trisubstituted arylphosphine oxide species by taking diphenyl(tert-butyl)phosphine as a substrate, belonging to the technical field of organic phosphine synthesis. The method comprises the following steps: with a transition metal palladium salt as a catalyst and a hydrazine compound and diphenyl(tert-butyl)phosphine as reaction substrates, adding the reaction substrates and an alkali compound into a reaction solvent, carrying out stirring and heating, conducting reacting for a certain period of time to obtain a reaction solution, and separating and purifying the reaction solution to obtain a trisubstituted arylphosphine oxide compound, wherein the hydrazine compound is any one selected from aromatic hydrazine and aromatic heterocyclic hydrazine; and the transition metal palladium salt catalyst is selected from any one of Pd(OAc)2, Pd(dba)2 and PdCl2. Compared with a traditional synthesis method, the method has the advantages that the use of diarylphosphine oxide hydrogen is avoided, raw materials are easy to obtain, reaction conditions are mild, yield is high, and reaction selectivity is good. In general, the method is friendly to environment and simple in synthesis process, and has certain industrial application prospects.

Description

technical field [0001] The invention belongs to the technical field of organic phosphine synthesis, and in particular relates to a method for synthesizing trisubstituted aryl phosphine oxide species with diphenyl tert-butyl phosphine as a substrate. Background technique [0002] Aromatic organophosphine compounds are widely used in various fields, among which, triarylphosphine oxide compounds are a very important class of chemicals, which play an important role in organic synthesis, polymer materials, photoelectric materials and catalytic coupling reactions. application value. At present, there have been many reports on the synthesis of triarylphosphine oxide compounds. Most of the traditional synthetic methods use diarylphosphine oxide hydrogen and various aryl coupling reagents to synthesize, such as: aryl boronic acid, aryl halide, benzene Nitrile etc. However, the synthesis of hydrogen diarylphosphine oxides is relatively difficult. In addition, compared with the C-H ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/53C07F9/58
CPCC07F9/5333C07F9/58
Inventor 耿巍芝李恒刘伟利
Owner XINXIANG RUNYU NEW MATERIAL TECH CO LTD
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