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

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*,

引用次数: 0

Abstract

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.