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Method for preparing phosphinic acid ester/phosphorous acid ester/phosphoric acid ester from P(O)-OH compound and aryl boronic acid

A technology of phosphinic acid and phosphinic acid is applied in chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, organic chemistry, etc., and can solve problems such as cumbersome experimental steps, harsh reaction conditions, and environmental pollution. To achieve the effect of simple and easy method, simple preparation and high yield

Active Publication Date: 2016-06-15
HUNAN INSTITUTE OF SCIENCE AND TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these methods generally use air-sensitive reagents (P(OR) 3 , carbon tetrachloride, sulfuryl chloride, etc.), and the experimental steps are cumbersome, the reaction conditions are harsh, the yield is low, and the pollution to the environment is relatively large

Method used

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  • Method for preparing phosphinic acid ester/phosphorous acid ester/phosphoric acid ester from P(O)-OH compound and aryl boronic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add 218mg (1.0mmol) of diphenylphosphoric acid, 122mg (1.0mmol) of phenylboronic acid, 120mg (2.0mmol) urea, 100mg molecular sieve and 28.7mg (0.2mmol) cuprous bromide into the Schlenk tube under oxygen atmosphere, Add 3.0ml of organic solvent (tetrahydrofuran, diethyl ether, toluene, 1,4-dioxane, N,N-dimethylformamide, dimethyl sulfoxide, acetonitrile) under an oxygen environment, at 80 o The reaction was stirred at C for 12 hours. Through GC detection and analysis, when acetonitrile is used as the reaction solvent, the productive rate of the coupling reaction can reach 92% productive rate.

Embodiment 2

[0027] 218 mg (1.0 mmol) of diphenylphosphoric acid, 122 mg (1.0 mmol) of phenylboronic acid, 2.0 mmol of base (triethylamine, sodium bicarbonate, potassium carbonate, sodium carbonate, urea, thiourea, cesium carbonate or potassium phosphate) , 100mg molecular sieve and 28.7mg (0.2mmol) cuprous bromide are added in the Schlenk tube under oxygen environment, add 3.0ml acetonitrile under oxygen environment, at 80 o The reaction was stirred at C for 12 hours. Through GC detection and analysis, when acetonitrile is used as the reaction solvent, the productive rate of the coupling reaction can reach 92% productive rate.

Embodiment 3

[0029] Mix 218mg (1.0mmol) of diphenylphosphoric acid, 122mg (1.0mmol) of phenylboronic acid, 120mg (2.0mmol) of urea, 100mg of additives (molecular sieves, phosphorus pentoxide, anhydrous sodium sulfate, anhydrous magnesium sulfate, anhydrous Calcium chloride (water) and 28.7mg (0.2mmol) cuprous bromide were added to the Schlenk tube under oxygen atmosphere, and 3.0ml acetonitrile was added under oxygen atmosphere, at 80 o The reaction was stirred at C for 12 hours. Through GC detection and analysis, when acetonitrile is used as the reaction solvent, the productive rate of the coupling reaction can reach 92% productive rate.

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Abstract

The invention provides a method for high-selectivity synthesis of phosphinic acid ester / phosphorous acid ester / phosphoric acid ester derivatives containing different substituted functional groups; a metal salt is used as a catalyst, a P(O)-OH-containing compound and aryl boronic acid are used as reactants, and an alkali, an additive and an organic solvent are added into the reaction system. The method has the advantages that the catalyst is cheap and easy to obtain; the reaction conditions are mild, and the method is safe and reliable; the selectivity of the obtained target product is close to 100%, and the yield is as high as 90% or more. The method solves the deficiency that traditional synthetic phosphinic acid ester / phosphorous acid ester / phosphoric acid ester compounds have poor reaction selectivity, complex reaction steps and low yield and need to use reagents harmful to the environment, and has a good prospect in industrial application. The invention also provides the corresponding phosphinic acid ester / phosphorous acid ester / phosphoric acid ester derivatives correspondingly containing different substituted functional groups.

Description

technical field [0001] The invention relates to the field of catalytic synthesis of organic phosphonate compounds, in particular to a method for preparing phosphinic acid / phosphinic acid / phosphate derivatives by using P(O)-OH compounds and aromatic boronic acid. Background technique [0002] Compounds such as organic phosphinates, phosphonites, and phosphates and their derivatives are an important class of organic compounds. These compounds have specific biological activity, good catalytic activity and optical activity, making them widely used in biology, medicine, etc. , Optically active materials and asymmetric catalytic synthesis have a wide range of applications. As we all know, it is difficult to find pure natural organic phosphinic acid / phosphinic acid / phosphate compounds in nature, and most phosphorus elements exist in nature in the form of inorganic salts (>70%). Most of the currently known organic phosphinic acid / phosphinic acid / phosphoric acid ester compounds a...

Claims

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Application Information

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IPC IPC(8): C07F9/32
CPCC07F9/3282
Inventor 唐课文熊碧权张盼良许卫凤
Owner HUNAN INSTITUTE OF SCIENCE AND TECHNOLOGY
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