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Synthesis of imines by hydroxylated o-phenanthroline copper complexes/O2-catalyzed oxidation of alcohols and cross-coupling of amines

A technology of amine cross-coupling and roline copper is applied in the field of alcohol and amine cross-coupling to synthesize imines, which can solve the problems of limiting final application and long reaction time, avoiding the use of nitroxide free radicals and bases, and achieving reaction selectivity. High and wide range of substrate effects

Active Publication Date: 2019-06-04
山西师范大学
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, additional base still needs to be added in the reaction, high temperature, long reaction time, and narrow range of alcohol substrates limit the final application of the complex as a catalyst

Method used

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  • Synthesis of imines by hydroxylated o-phenanthroline copper complexes/O2-catalyzed oxidation of alcohols and cross-coupling of amines
  • Synthesis of imines by hydroxylated o-phenanthroline copper complexes/O2-catalyzed oxidation of alcohols and cross-coupling of amines
  • Synthesis of imines by hydroxylated o-phenanthroline copper complexes/O2-catalyzed oxidation of alcohols and cross-coupling of amines

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Add 50μL (0.5mmol) benzyl alcohol, 65μL (0.6mmol) benzidine, 0.0065g (0.0125mmol) Cu 2 (ophen) 2 , 2mL DMF were sequentially added to a 10mL round-bottomed flask, in a standard atmospheric pressure O 2 Reaction for 12 hours in the atmosphere at room temperature. Detected by gas chromatography (HP-5 capillary column, using nitrogen as carrier gas flow rate is 1.0mL / min, column temperature: initial temperature 40℃ (maintain 4min), increase temperature at 20℃ / min to 285℃ (maintain 2min), enter Sample port temperature: 270°C, detector temperature: 300°C), the conversion rate of benzyl alcohol was 92%, and the yield of the product N-benzylbenzaldehyde imine was 90%.

Embodiment 2

[0019] In Example 1, the benzyl alcohol used was replaced with equimolar 4-methylthiobenzyl alcohol, and the other steps were the same as in Example 1. The conversion rate of 4-methylthiobenzyl alcohol was 99% by gas chromatography. The yield of N-benzyl-4-methylthiobenzaldehyde imine was 97%.

Embodiment 3

[0021] In Example 1, the benzyl alcohol used was replaced with an equimolar 4-methoxybenzyl alcohol, and the other steps were the same as in Example 1. The conversion rate of 4-methoxybenzyl alcohol was 89% by gas chromatography. The yield of N-benzyl-4-methoxybenzaldehyde imine was 88%.

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Abstract

The invention discloses a method for synthesizing imine through cross-coupling of hydroxylation phenanthroline copper complex / O2 catalytic oxidation alcohol and amine. According to the method, an economical and cheap hydroxylation phenanthroline copper complex is selected as a catalyst, green O2 is selected as an oxidizing agent, cross-coupling of alcohol and amine is realized under the condition of normal temperature, alkali and an expensive free radical of nitroxide is prevented from being used, and a series of imine compounds are successfully prepared. The method provided by the invention is high in reaction selectivity and relatively wide in a substrate application range, and has a great industrial application potential.

Description

Technical field [0001] The invention belongs to the technical field of the cross-coupling of alcohols and amines to synthesize imines, and specifically relates to a hydroxylated copper o-phenanthroline complex as a catalyst, and a green O 2 As an oxidant, it catalyzes the cross-coupling reaction of oxidized alcohol and amine to synthesize imine. Background technique [0002] Imines, also known as Schiff bases, are a kind of very important organic synthesis intermediates containing C=N unsaturated double bonds. Because organic reactions such as cyclization, reduction, addition, and condensation can occur, they can further construct drugs. , Industrial, biological and natural products. Therefore, people have always been interested in the synthesis and application of imines. [0003] Traditionally, imines are generally formed by the condensation of carbonyl compounds (aldehydes or ketones) with primary amines. In this process, dehydrating agent and Lewis acid are often needed as cat...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C249/02C07C251/24C07C251/16C07C251/18C07C319/20C07C323/45C07D213/53C07D307/52
CPCC07C249/02C07C319/20C07D213/53C07D307/52C07C251/24C07C251/16C07C251/18C07C323/45
Inventor 张玲娟刘捷张献明
Owner 山西师范大学
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