4-羟基苯甲醛催化过氧化氢活化未活化烯烃的绿色环氧化反应

IF 9.2 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Green Chemistry Pub Date : 2025-08-14 DOI:10.1039/d5gc02537k

Efthymios T. Poursaitidis , Christiana Mantzourani , Ierasia Triandafillidi , Maroula G. Kokotou , Christoforos G. Kokotos

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引用次数: 0

摘要

在寻求绿色、廉价和可持续的方法来环氧化未活化的烯烃，为学术和工业应用，对过氧化氢的有效有机催化活化剂的兴趣越来越受到重视。在这项工作中，我们报告了一种商业上可用的醛，4-羟基苯甲醛的创新用途，作为H2O2的有效活化剂，在亚化学计量量（20摩尔%）下选择性环氧化烯烃。大量的烯烃被选择性环氧化，收率很高。深入的机制研究揭示了一种涉及Payne/Dakin串联途径的新型复杂环氧化机制。4-羟基苯甲醛似乎主要转化为对苯二酚/苯醌，它们已被发现是过氧化氢环氧化烯烃的有效活化剂。这一迄今尚未确定的氧化途径可能为氧化转化找到新的潜在应用。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Green epoxidation of unactivated alkenes via the catalytic activation of hydrogen peroxide by 4-hydroxybenzaldehyde

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Green epoxidation of unactivated alkenes via the catalytic activation of hydrogen peroxide by 4-hydroxybenzaldehyde

In the quest for green, inexpensive and sustainable methods for the epoxidation of unactivated alkenes, for both academic and industrial applications, the interest in effective organocatalytic activators of hydrogen peroxide is gaining increased attention. In this work, we report the innovative use of a commercially available aldehyde, 4-hydroxybenzaldehyde, as an effective activator of H₂O₂ in a substoichiometric amount (20 mol%) for the selective epoxidation of alkenes. A plethora of alkenes were selectively epoxidised in very good to high yields. Thorough mechanistic studies revealed a novel, complex epoxidation mechanism involving a Payne/Dakin tandem pathway. 4-Hydroxybenzaldehyde seems to be mainly converted to hydroquinone/benzoquinone, which have been uncovered as efficient activators of hydrogen peroxide for the epoxidation of alkenes. This so far unidentified oxidative pathway may find new potential applications for oxidative transformations.

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来源期刊

Green Chemistry 化学-化学综合

CiteScore

16.10

自引率

7.10%

发文量

677

审稿时长

1.4 months

期刊介绍： Green Chemistry is a journal that provides a unique forum for the publication of innovative research on the development of alternative green and sustainable technologies. The scope of Green Chemistry is based on the definition proposed by Anastas and Warner (Green Chemistry: Theory and Practice, P T Anastas and J C Warner, Oxford University Press, Oxford, 1998), which defines green chemistry as the utilisation of a set of principles that reduces or eliminates the use or generation of hazardous substances in the design, manufacture and application of chemical products. Green Chemistry aims to reduce the environmental impact of the chemical enterprise by developing a technology base that is inherently non-toxic to living things and the environment. The journal welcomes submissions on all aspects of research relating to this endeavor and publishes original and significant cutting-edge research that is likely to be of wide general appeal. For a work to be published, it must present a significant advance in green chemistry, including a comparison with existing methods and a demonstration of advantages over those methods.