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Method for preparing phenol by performing catalytic oxidation on aryl boron compound

A technology for catalytic oxidation and hydrazine compounds, applied in the preparation of organic compounds, preparation of amino hydroxyl compounds, chemical instruments and methods, etc., can solve the problem of expensive and unused heterocyclic aromatic boron reactants and flavins Solve problems such as complex salt structure, achieve high selectivity, cheap catalyst, and stable substrate source

Inactive Publication Date: 2014-07-23
NANJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It has been reported that air or oxygen is used as an oxidizing agent to oxidize aromatic boron compounds to produce phenols, but either metal palladium, ruthenium and copper are required, or a large amount of organic promoter is required to make the reaction go smoothly
Recently, there are literatures that use flavin salt as catalyst, metered hydrazine hydrate as reducing agent, and oxygen as oxidizing agent to oxidize aromatic boron compounds to produce phenol. The reaction effect is good, but this method has not been used and has more application value. Heterocyclic aromatic boron reactant, and flavin salt structure is complex and expensive (Radek Cibulka et al., Org. Biomol. Chem., 2014,12, 2137-2142)
[0004] Up to now, a kind of method that does not need the participation of metal, cheap and easy-to-obtain catalyst to catalyze air or oxygen to oxidize aryl boron compounds to prepare phenol has not been reported

Method used

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  • Method for preparing phenol by performing catalytic oxidation on aryl boron compound
  • Method for preparing phenol by performing catalytic oxidation on aryl boron compound
  • Method for preparing phenol by performing catalytic oxidation on aryl boron compound

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Embodiment 1

[0030] Compound 1: Hydrazine hydrate (0.25mmol), phenylboronic acid (0.5mmol), cesium carbonate (1.0mmol) and polyethylene glycol-600 (2.0g) were sequentially added into a 25mL reaction flask. mixture at 80 o Under C, open the reaction until the raw material is completely reacted. The reaction mixture was cooled to room temperature, the solvent was evaporated under reduced pressure, and the product was separated by column chromatography with a yield of 96%.

Embodiment 2

[0032] Compound 2: Hydrazine hydrate (0.25mmol), 2-methoxyphenylboronic acid (0.5mmol), cesium carbonate (1.0mmol) and polyethylene glycol-400 (2.0g) were sequentially added into a 25mL reaction flask. mixture at 80 o Under C, open the reaction until the raw material is completely reacted. The reaction mixture was cooled to room temperature, the solvent was distilled off under reduced pressure, and the product was separated by column chromatography with a yield of 99%.

Embodiment 3

[0034] Compound 3: Hydrazine hydrate (0.25mmol), 4-methoxyphenylboronic acid (0.5mmol), cesium carbonate (1.0mmol) and polyethylene glycol-600 (2.0g) were sequentially added into a 25mL reaction flask. mixture at 100 o Under C, open the reaction until the raw material is completely reacted. The reaction mixture was cooled to room temperature, the solvent was distilled off under reduced pressure, and the product was separated by column chromatography with a yield of 99%.

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Abstract

The invention discloses a method for synthesizing a phenolic compound by performing catalytic oxidation on an aryl boron compound. The method comprises the steps of adding a hydrazine hydrate or hydrazine compound catalyst into a solvent namely alcohol or an aqueous solution of alcohol under the action of alkali, and performing catalytic oxidation on the aryl boron compound to directly prepare the phenolic compound. According to the method for preparing the phenolic compound, disclosed by the invention, the catalyst is a cheap hydrazine hydrate or hydrazine compound; an oxidant is air or oxygen under normal pressure; a reaction does not need a metal catalyst, and is good in activity; a substrate is wide and stable in sources; sensitive functional groups of the substrate are good in compatibility and wide in application range. Under the optimized reaction conditions, the separation yield of target products reaches 99%.

Description

technical field [0001] The invention relates to a method for preparing phenol, in particular to a method for directly using air or oxygen as an oxidant to catalyze and oxidize aromatic boron compounds to prepare phenol. Background technique [0002] Phenolic compounds are important intermediates in organic synthesis, and their basic structural units exist in the molecular structures of a large number of natural products, medicines and materials, and are widely used in the fields of biology, medicine and materials. Methods for synthesizing such substances have attracted extensive attention and some progress has been made. Among them, aryl boron compounds as raw materials for the production of phenols have attracted widespread attention, because aryl boron compounds have a wide range of sources, high selectivity in the reaction, stability to air and water, and easy separation from the product after the reaction. [0003] At present, there are two main methods for producing ph...

Claims

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Application Information

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IPC IPC(8): C07B41/02C07C39/04C07C37/01C07C43/23C07C41/26C07C39/07C07C215/76C07C213/00C07C43/295C07C39/27C07C39/24C07C255/53C07C253/30C07C205/22C07C205/23C07C201/12C07C69/84C07C67/31C07C39/14C07C205/25C07D213/64C07D213/68C07D213/85C07D215/22C07D215/28C07D217/24C07D217/02C07D333/32C07D333/38C07D231/54C07D307/58C07D307/91C07D207/36C07D209/08C07D263/40C07D263/54C07D333/76C07D277/62C07D401/04C07D235/06C07D241/18C07D241/42C07D237/14C07D239/36C07D263/32
CPCY02P20/52
Inventor 韩维黄峥袁林新顾文超邵晔
Owner NANJING NORMAL UNIVERSITY