单线态氧制备醛的Nef反应的发展及其机理研究

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-04-17 DOI:10.1021/acs.orglett.5c0095410.1021/acs.orglett.5c00954

Ira Novita Sari, Bobo Yan, Tatsuya Morozumi, Yuichi Kamiya and Taiki Umezawa*,

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引用次数: 0

摘要

描述了硝基化合物转化为醛的Nef反应。各种官能团，如醚、硅醚、缩醛或酯，可以在Cs2CO3和单线态氧作为氧化剂的情况下以高收率生成醛。在一锅操作中实现了硝基甲基向羟甲基的转化。利用离子色谱法和自由基清除剂研究了Nef反应的机理，提出了两种独特的反应途径。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Development and Mechanistic Insights into Nef Reaction for Preparation of Aldehydes Using Singlet Oxygen

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Development and Mechanistic Insights into Nef Reaction for Preparation of Aldehydes Using Singlet Oxygen

The Nef reaction for conversion of nitro compounds to aldehydes is described. Various functional groups, such as ethers, silyl ethers, acetals or esters, were tolerated to give aldehydes in high yields using Cs₂CO₃ and singlet oxygen as an oxidant. Transformations of nitromethyl groups into hydroxymethyl groups were achieved in a one-pot operation. The mechanism involved in the Nef reaction was studied using ion chromatography and radical scavengers, which resulted in the proposal of two unique reaction pathways.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.