异丙醇流动光还原硝基（杂）芳烃制（杂）芳基羟胺：在扑热息痛合成中的应用。

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-09-19 DOI:10.1021/acs.joc.5c01710

Pierre Nabokoff, , , Joannah Ngompaza-Diarra, , , Julien Boutet, , , Jean-Marc Paris*, , and , Janine Cossy*,

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引用次数: 0

摘要

用iPrOH光还原取代硝基（杂）芳烃已在间歇和连续流化学中实现。硝基苯被吸电子基团取代时，N-（杂）芳基羟胺的产率较高。该反应具有化学选择性，因为腈、酯、羧酸、酮和卤化物不会被还原。硝基苯光还原合成扑热息痛是通过n -苯基羟胺的乙酰化和原1,5重排来实现的。

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Photoreduction of Nitro (Hetero)arenes to (Hetero)arylhydroxylamines by isoPropanol in Flow: Application to the Synthesis of Paracetamol

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Photoreduction of Nitro (Hetero)arenes to (Hetero)arylhydroxylamines by isoPropanol in Flow: Application to the Synthesis of Paracetamol

The photoreduction of substituted nitro (hetero)arenes by iPrOH has been achieved in batch and continuous flow chemistry. Good yields of N-(hetero)arylhydroxylamines were obtained when nitrobenzene was substituted by electron-withdrawing groups. The reaction is chemoselective as nitriles, esters, carboxylic acids, ketones, and halides are not reduced. The application of the photoreduction of nitrobenzene to the synthesis of paracetamol was achieved by the acetylation of N-phenylhydroxylamine followed by an original 1,5-rearrangement.

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.