Oxidative decarboxylation of arylacetic acids and arylacetic esters with singlet molecular oxygen generated from trans-5-hydroperoxy-3,5-dimethyl-1,2-dioxolan-3-yl ethaneperoxate

IF 1.7 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Journal of Chemical Sciences Pub Date : 2024-02-12 DOI:10.1007/s12039-023-02243-5

Z Najminejad

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Abstract

An efficient method for the oxidative decarboxylation of arylacetic acids and arylacetic esters using trans-5-hydroperoxy-3,5-dimethyl-1,2-dioxolane-3-yl ethaneperoxate in combination with KOH as base is reported. The decarboxylation of carboxylic acids and their derivatives was efficiently achieved with singlet molecular oxygen. Singlet molecular oxygen was produced in situ from the fragmentation of the trans-5-hydroperoxy-3,5-dimethyl-1,2-dioxolane-3-yl ethaneperoxate in the presence of KOH, and it has been explored as an effective oxidant for oxidative decarboxylation of arylacetic acids. Further investigation showed that the reaction also permits the synthesis of aromatic ketones by oxidative decarboxylation of arylacetic esters.

Graphical abstract

An efficient method for the oxidative decarboxylation of arylacetic acids and arylacetic esters is reported.The decarboxylation of carboxylic acids and their derivatives were efficiently achieved with singlet molecular oxygen. Singlet molecular oxygen was produced insitu from fragmentation of the trans-5-hydroperoxy-3,5-dimethyl-1,2- dioxolane-3-yl ethaneperoxate in the presence of KOH, and it has been explored as an effective oxidant for oxidative decarboxylation of arylacetic acids and arylacetic esters.

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反式-5-氢过氧-3,5-二甲基-1,2-二氧戊环-3-基乙内酯产生的单线态分子氧对芳基乙酸和芳基乙酸酯的氧化脱羧作用

报告中介绍了一种使用反式-5-氢过氧-3,5-二甲基-1,2-二氧戊环-3-基乙醇过氧化物与 KOH 作为碱对芳基乙酸和芳基乙酸酯进行氧化脱羧的高效方法。利用单线态分子氧有效地实现了羧酸及其衍生物的脱羧反应。在 KOH 存在下，反式-5-氢过氧-3,5-二甲基-1,2-二氧戊环-3-乙内过氧乙酸酯在原位碎裂产生单线态分子氧，并将其作为一种有效的氧化剂用于芳基乙酸的氧化脱羧反应。进一步的研究表明，该反应还可以通过芳基乙酸酯的氧化脱羧合成芳香酮。单线分子氧是反式-5-氢过氧-3,5-二甲基-1,2-二氧戊环-3-基乙醇过氧化物在 KOH 的存在下碎裂而产生的，它已被探索用作芳基乙酸和芳基乙酸酯氧化脱羧的有效氧化剂。

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来源期刊

Journal of Chemical Sciences CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

3.10

自引率

5.90%

发文量

107

审稿时长

1 months

期刊介绍： Journal of Chemical Sciences is a monthly journal published by the Indian Academy of Sciences. It formed part of the original Proceedings of the Indian Academy of Sciences – Part A, started by the Nobel Laureate Prof C V Raman in 1934, that was split in 1978 into three separate journals. It was renamed as Journal of Chemical Sciences in 2004. The journal publishes original research articles and rapid communications, covering all areas of chemical sciences. A significant feature of the journal is its special issues, brought out from time to time, devoted to conference symposia/proceedings in frontier areas of the subject, held not only in India but also in other countries.