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Method for synthesizing biaryl compound

A compound, biaryl technology, applied in the field of organic synthesis, can solve the problems of poor selectivity, low efficiency and poor practicability

Pending Publication Date: 2021-09-10
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these reported methods suffer from low efficiency, poor selectivity and poor practicability

Method used

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  • Method for synthesizing biaryl compound
  • Method for synthesizing biaryl compound
  • Method for synthesizing biaryl compound

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0018] Add 0.3mmol organoantimony compound 13a (R 7 = Ph; R 1 =4-Me), 0.3 mmol iodobenzene 18a (R 2 =H), 0.015 mmol of palladium acetate, 0.03 mmol of tetrabutylphosphine bromide, 0.6 mmol of cesium carbonate, 40 μL of water and 2.0 mL of tetrahydrofuran (THF), reacted at 110° C. for 12 h. After the reaction was completed, the solvent was removed under reduced pressure, and the pure compound was separated by column chromatography with a yield of 90%.

preparation example 2

[0020] Add 0.3mmol organoantimony compound 13b (R 7 = Et; R 1 =4-Me), 0.3 mmol iodobenzene 18a (R 2 =H), 0.015 mmol of palladium acetate, 0.03 mmol of tetra-n-butylphosphine bromide, 0.6 mmol of cesium carbonate, 40 μL of water and 2.0 mL of tetrahydrofuran (THF), reacted at 110° C. for 12 h. After the reaction was completed, the solvent was removed under reduced pressure, and the pure compound was separated by column chromatography with a yield of 92%.

preparation example 3

[0022] Add 0.3mmol organoantimony compound 13c (R 7 = Et; R 1 =3-Me), 0.3 mmol iodobenzene 18a (R 2 =H), 0.015 mmol of palladium acetate, 0.03 mmol of tetra-n-butylphosphine bromide, 0.6 mmol of cesium carbonate, 40 μL of water and 2.0 mL of tetrahydrofuran (THF), reacted at 110° C. for 12 h. After the reaction was completed, the solvent was removed under reduced pressure, and the pure compound was separated by column chromatography with a yield of 85%.

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Abstract

The invention aims to provide a method for synthesizing a biaryl compound. The catalytic synthesis method is characterized in that palladium acetate is used as a catalyst, a cyclic organic antimony compound is used as a nucleophilic reagent, aryl bromide or aryl iodide is used as an electrophilic reagent, tetrahydrofuran is used as a solvent, and the biaryl compound is synthesized through direct cross coupling under the condition of an air atmosphere. The method has the advantages of high yield, high selectivity, simplicity and convenience in operation and the like.

Description

【Technical field】 [0001] The invention relates to the field of organic synthesis, and relates to a method for synthesizing biaryl compounds, in particular to a method for synthesizing biaryl compounds through highly selective cross-coupling of organic antimony compounds and halogenated aromatic hydrocarbons under the condition of palladium acetate as a catalyst. 【Background technique】 [0002] Transition metal-catalyzed cross-coupling reactions are one of the most powerful methods for the synthesis of biaryls. Typically, such reactions involve cross-coupling reactions of organometallic nucleophiles (including organolithium, organomagnesium, organozinc, organotin, organosilicon, and organoboron) with organic electrophiles. In order to improve the practicality and efficiency of cross-coupling reactions, chemists are striving to develop highly efficient organometallic reagents. Recently, organoindium reagents, organomanganese reagents, organotitanium reagents, organobismuth re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C1/00C07C15/14C07C41/30C07C43/205C07C45/68C07C47/546C07C49/782C07C67/343C07C69/78C07C17/263C07C22/08C07C253/30C07C255/50C07F7/08C07C15/50C07C201/12C07C205/06
CPCC07C1/00C07C41/30C07C45/68C07C67/343C07C17/263C07C253/30C07F7/0805C07C201/12C07C15/14C07C43/205C07C47/546C07C49/782C07C69/78C07C43/2055C07C22/08C07C255/50C07C15/50C07C205/06
Inventor 邱仁华张德奖徐芝尹双凤神户宣明
Owner HUNAN UNIV
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