钯催化芳基硼酸和醛的反应研究
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摘要
芳基硼酸具有低毒,良好的热稳定性,官能团兼容性以及对水、空气不敏感等优点。近年来,芳基硼试剂和醛类化合物的反应研究受到了有机化学工作者的青睐。本文围绕这一主题进行相关的有机合成研究。本论文首先综述了近年来金属催化芳基硼酸和醛的反应,并研究和探讨了不同体系中钯催化芳基硼酸和醛的三个化学反应及其应用：(1)发展了钯/1-三萘基膦体系催化芳基以及杂芳基硼酸对醛的加成反应来合成甲醇衍生物的方法。该方法具有高效、良好的官能团兼容性以及对水和空气不敏感的优点；(2)通过钯催化芳基硼酸与醛偶联类型的反应,“一锅法”合成二芳基甲酮的衍生物。机理研究表明产物可能涉及两步反应：首先是芳基硼酸对醛的加成生成二芳基甲醇,然后氧化二芳基甲醇得到二芳基甲酮：(3)通过钯催化芳基硼酸对醛的酯化反应,方便地合成了芳基苯甲酸酯的衍生物。研究表明氧分子参与了反应并在反应过程中起到了重要作用。
以上研究为合成甲醇类衍生物、二芳基甲酮类衍生物以及芳基苯甲酸酯类衍生物提供了新的方法。反应原料易得,操作简便,条件温和,产率从中到优。
In view of the advantages of arylboronic acids, that is, low toxicity, good functional group-tolerance, stability to air or moisture,great attention has been paid to the reactions between arylboronic acids and aldehydes in recent years.In this paper, recent advances in the metal-catalyzed reactions between arylboronic acids and aldehydes were first reviewed, then three this kind of reactions were studied:(1)A palladium/trinaphthalen-1-ylphosphine-catalyzed synthesis of carbinol derivatives using aryl- or heteroarylboronic acids and aldehydes is described.This route enjoys high efficiency,good functional group compatibility and air/moisture tolerance;(2)One-pot synthesis of diaryl ketones from aldehydes via palladium-catalyzed coupling-type reaction with arylboronic acids.A cascade addition/oxidation procedure is proposed, in which diaryl ketones are produced from the corresponding diarylmethanols formed in situ by addition reaction between arylboronic acids and aldehydes in one-pot;(3)A palladium-catalyzed aromatic-esterification of aldehydes with arylboronic acids for the synthesis of aryl benzoate derivatives is reported.Mechanistic studies show that oxygen molecule takes part in this reaction and is essential for this transformation.
The new approaches for the synthesis of carbinol derivatives,diaryl ketone derivatives, and aryl benzoate derivatives are developed, which enjoy the advantages of mild reaction conditions, simple operation, moderate to high yields,and commercially available materials.
以上研究为合成甲醇类衍生物、二芳基甲酮类衍生物以及芳基苯甲酸酯类衍生物提供了新的方法。反应原料易得,操作简便,条件温和,产率从中到优。
In view of the advantages of arylboronic acids, that is, low toxicity, good functional group-tolerance, stability to air or moisture,great attention has been paid to the reactions between arylboronic acids and aldehydes in recent years.In this paper, recent advances in the metal-catalyzed reactions between arylboronic acids and aldehydes were first reviewed, then three this kind of reactions were studied:(1)A palladium/trinaphthalen-1-ylphosphine-catalyzed synthesis of carbinol derivatives using aryl- or heteroarylboronic acids and aldehydes is described.This route enjoys high efficiency,good functional group compatibility and air/moisture tolerance;(2)One-pot synthesis of diaryl ketones from aldehydes via palladium-catalyzed coupling-type reaction with arylboronic acids.A cascade addition/oxidation procedure is proposed, in which diaryl ketones are produced from the corresponding diarylmethanols formed in situ by addition reaction between arylboronic acids and aldehydes in one-pot;(3)A palladium-catalyzed aromatic-esterification of aldehydes with arylboronic acids for the synthesis of aryl benzoate derivatives is reported.Mechanistic studies show that oxygen molecule takes part in this reaction and is essential for this transformation.
The new approaches for the synthesis of carbinol derivatives,diaryl ketone derivatives, and aryl benzoate derivatives are developed, which enjoy the advantages of mild reaction conditions, simple operation, moderate to high yields,and commercially available materials.
引文
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