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Preparation method for aromatic phosphine compound

A technology for aromatic phosphine compounds, which is applied in the field of preparation of aromatic phosphine compounds, and achieves the effects of mild reaction conditions, good industrial application prospects, superior conversion rate and yield

Inactive Publication Date: 2017-05-10
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the realization of these works depends on the catalytic system composed of noble metals such as palladium and silver, and there are few reports on the arylation of aromatic phosphines catalyzed by ortho-position carbon-hydrogen bonds with cheap metals.

Method used

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  • Preparation method for aromatic phosphine compound
  • Preparation method for aromatic phosphine compound
  • Preparation method for aromatic phosphine compound

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0027] Add 0.005mmol copper powder, 0.1mmol P,P-diphenyl-N-(8-aminoquinoline)-phosphonamide, 0.2mmol phenylboronic acid in turn to the Schlenk reaction tube, vacuum backfill oxygen; dropwise under oxygen atmosphere 1mL of acetonitrile was used as a solvent, and the reaction was continued at 100°C for 6h; after the reaction was completed, it was cooled to room temperature and separated by column chromatography to obtain the target product: P-(2-phenylphenyl)-P-phenyl-N-(8 -aminoquinoline)-phosphonamide in 93% yield.

preparation example 2

[0029] Add 0.005mmol cuprous oxide, 0.1mmol P,P-diphenyl-N-(8-aminoquinoline)-phosphonamide, and 0.2mmol phenylboronic acid in turn to the Schlenk reaction tube, vacuum backfill oxygen; drop under oxygen atmosphere Add 1mL of acetonitrile as a solvent, and continue to react at 100°C for 6h; after the reaction, cool to room temperature and separate by column chromatography to obtain the target product: P-(2-phenylphenyl)-P-phenyl-N-( 8-aminoquinoline)-phosphonamide in 91% yield.

preparation example 3

[0031] Add 0.005mmol copper chloride, 0.1mmol P,P-diphenyl-N-(8-aminoquinoline)-phosphonamide, 0.1mmol phenylboronic acid in turn to the Schlenk reaction tube, vacuum backfill oxygen; drop under oxygen atmosphere Add 1mL of acetonitrile as a solvent, and continue to react at 100°C for 6h; after the reaction, cool to room temperature and separate by column chromatography to obtain the target product: P-(2-phenylphenyl)-P-phenyl-N-( 8-aminoquinoline)-phosphonamide in 92% yield.

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Abstract

The invention discloses a preparation method for an aromatic phosphine compound. The method is a new method for realizing arylation of ortho-position C-H bond of the aromatic phosphine compound in high yield and selectivity. In the oxygen atmosphere, copper is used as a catalyst, P,P-diaryl-N-(8-aminoquinoline)-phosphamide is used as a raw material, and an aryl boronic acid is used as an aryl source. The method is capable of realizing the arylation of the ortho-position C-H bond of the aromatic phosphine compound catalyzed by cheap metal. The reaction condition is moderate, the operation is easy, the preparation process is green and environmental, and the conversion rate and productive rate of a target product are high. The problems in other synthetic methods that the reaction temperature is higher, the precious metal catalyst is used necessarily, more wastes are produced and the environment pollution is easily caused and so on can be solved, and the method has good industrial application prospect.

Description

[0001] 【Technical field】 [0002] The invention relates to the field of organic synthesis, in particular to a preparation method of aromatic phosphine compounds. [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 defects such as high reaction tempe...

Claims

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Application Information

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IPC IPC(8): C07F9/60
CPCC07F9/60
Inventor 尹双凤雷健邱仁华彭尧
Owner HUNAN UNIV
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