Copper-Catalyzed One-Pot Protocol for Reductive N-Arylation of Nitroarenes with (Hetero)aryl Chlorides in Water

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-12-09 DOI:10.1021/acs.orglett.4c03753

Peng Hong, Lifang Wang, Xinhai Zhu, Manna Huang, Yiqian Wan

引用次数: 0

Abstract

A novel protocol for the Cu-catalyzed reductive N-arylation of nitroarenes with (hetero)aryl chlorides in water has been realized. Combining N-(9H-carbazol-9-yl)-6-hydroxypicolinamide (L2) with oxalohydrazide is vital to realize the method at 90 °C with a loading of 5 mol % of Cu₂O/L2. Various nitroarenes and aryl chlorides have been successfully coupled in good to excellent isolated yields. Further, two diarylamine-containing key intermediates, 3f and 4u, have been smoothly synthesized on a gram scale using this method.

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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.