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Alpha-benzyl-modified diaryl phosphonic compound and preparation method thereof

A technology of aryl phosphines and compounds, applied in the field of organic synthesis, to achieve the effect of wide application range and high selectivity of substrates

Active Publication Date: 2017-08-18
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the construction of aromatic phosphine compounds modified by inert groups can only be carried out by means of traditional coupling methods based on organohalogen reagents.

Method used

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  • Alpha-benzyl-modified diaryl phosphonic compound and preparation method thereof
  • Alpha-benzyl-modified diaryl phosphonic compound and preparation method thereof
  • Alpha-benzyl-modified diaryl phosphonic compound and preparation method thereof

Examples

Experimental program
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Effect test

preparation example 1

[0032] Add 0.005mmol copper powder and 0.1mmol P,P-diphenyl-N-(8-aminoquinoline)-phosphonamide into a 25mL Schlenk reaction tube, vacuum backfill nitrogen 5 times; under nitrogen atmosphere, add toluene in sequence and di-tert-butyl peroxide (DTBP), continue to react at 100°C for 24h; after the reaction is completed, cool to room temperature and separate by column chromatography to obtain the target product I; the reaction result is: P-(2-benzylphenyl )-P-phenyl-N-(8-aminoquinoline)-phosphonamide, the productive rate is 93%; Get P-(2-benzylphenyl)-P-phenyl-N-(8-aminoquinoline Phenyl)-phosphonamide was placed in a 25mL Schlenk reaction tube, followed by adding 2mol / L aqueous sodium hydroxide solution and ethanol, and reacted vigorously at 80°C for 2h; after the reaction was completed, it was cooled to room temperature and separated by column chromatography to obtain the target product P-(2-benzylphenyl)-P-phenyl-N-(8-aminoquinoline)-phosphonic acid, the yield is 92%; take P-(2-...

preparation example 2

[0034] Add 0.01mmol cuprous oxide and 0.1mmol P,P-diphenyl-N-(8-aminoquinoline)-phosphonamide into a 25mL Schlenk reaction tube, vacuum backfill nitrogen 5 times; under nitrogen atmosphere, add P-xylene and tert-butyl hydroperoxide (TBHP), continue to react at 100°C for 24h; after the reaction is completed, cool to room temperature and separate by column chromatography to obtain the target product I; the reaction result is: P-[2-( 4-methylbenzyl) phenyl]-P-phenyl-N-(8-aminoquinoline)-phosphonamide, the productive rate is 98%; P-[2-(4-methylbenzyl)benzene Base]-P-phenyl-N-(8-aminoquinoline)-phosphonamide was placed in a 25mL Schlenk reaction tube, and 2mol / L sodium hydroxide aqueous solution and ethanol were added successively, and reacted violently at 80°C for 2h; Cool to room temperature after completion, and separate by column chromatography to obtain the target product P-[2-(4-methylbenzyl)phenyl]-P-phenyl-N-(8-aminoquinoline)-phosphonic acid, The yield rate is 90%; P-[2-(...

preparation example 3

[0036]Add 0.015mmol copper chloride, 0.1mmol P,P-diphenyl-N-(8-aminoquinoline)-phosphonamide into a 25mL Schlenk reaction tube, vacuum backfill nitrogen 5 times; under nitrogen atmosphere, add Toluene and hydrogen peroxide continued to react at 100°C for 24 hours; after the reaction was completed, cooled to room temperature and separated by column chromatography to obtain the target product I; the reaction result was: P-[2-(3-methylbenzyl)phenyl] -P-phenyl-N-(8-aminoquinoline)-phosphonamide, the productive rate is 99%; Take P-[2-(4-methylbenzyl) phenyl]-P-phenyl-N- (8-Aminoquinoline)-phosphonamide was placed in a 25mL Schlenk reaction tube, followed by adding 2mol / L sodium hydroxide aqueous solution and ethanol, and reacted vigorously at 80°C for 2h; after the reaction was completed, cooled to room temperature and separated by column chromatography , to obtain the target product P-[2-(3-methylbenzyl) phenyl]-P-phenyl-N-(8-aminoquinoline)-phosphonic acid, the productive rate is...

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Abstract

The invention discloses an alpha-benzyl-modified diaryl phosphonic compound and a preparation method thereof. The method is a novel method for preparing a mono-substituted benzyl phosphamide compound from a copper salt as a catalyst, P,P-diaryl-N-(8-aminoquinoline) phosphamide as a raw material, methylbenzene and a derivative thereof as a solvent and a benzyl source and peroxide as an oxidizing agent under a nitrogen condition at high yield and high selectivity. Corresponding alpha-benzylated arylphosphonic acid and alpha-benzylated aryl hydrogen phosphonate can be prepared from alpha-benzylated aryl phsophonamidate through adding alkali and a reducing agent. The method is simple in reaction condition, easy to operate, low in cost, green and environmentally friendly in preparation process, high in conversion rate and yield of a target product; the target product can be prepared at high yield after the reaction scale is amplified by 50 times; and the alpha-benzyl-modified diaryl phosphonic compound has a good industrial application prospect.

Description

[0001] 【Technical field】 [0002] The invention relates to the field of organic synthesis, in particular to a class of α-benzyl modified diarylphosphine compounds and a preparation method thereof. [0003] 【Background technique】 [0004] Aromatic phosphine compounds are important raw materials and intermediates in organic synthesis. They have a variety of unique properties and have important application values ​​in various fine chemical fields such as organic synthesis, catalysis, medicine, materials, and pesticides. The traditional methods for preparing aromatic phosphine compounds mainly include: transition metal-catalyzed coupling reaction between organohalogen reagents and phosphine hydrogen compounds and nucleophilic substitution reactions between organometallic reagents (Grignard reagents or organolithium reagents) and phosphonate or phosphine halide compounds. Due to the use of organohalogen reagents, the traditional method for preparing aromatic phosphine compounds has ...

Claims

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Application Information

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IPC IPC(8): C07F9/30C07F9/53C07F9/60
CPCC07F9/304C07F9/5325C07F9/60
Inventor 邱仁华雷健尹双凤彭尧
Owner HUNAN UNIV
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