Palladium-Catalyzed Aminocarbonylation Using Nitroarenes under NMP-Mediated Photochemical Conditions

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-06-13 DOI:10.1021/acs.orglett.5c01619

Minwoo Park, Karthik Rajan Rajamanickam, Sunwoo Lee

引用次数: 0

Abstract

A photochemical approach enabling mild amide synthesis from aryl iodides, carbon monoxide, and nitroarenes at 25 °C under 1 atm of CO is disclosed. Under a PdCl₂/Xantphos–FeCl₃ catalyst in N-methylpyrrolidone, broad functional group tolerance is observed. Mechanistic studies reveal that nitroarenes form a base-activated N-methylpyrrolidone-bound adduct, which generates an aniline-like intermediate that couples with the acyl–palladium complex to deliver the desired amides.

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在nmp介导的光化学条件下钯催化硝基芳烃氨基羰基化

本发明公开了一种光化学方法，可以在25°C下，在1atm CO下由芳基碘化物、一氧化碳和硝基芳烃合成温和的酰胺。在n -甲基吡咯烷酮的PdCl2/ Xantphos-FeCl3催化剂下，观察到广泛的官能团耐受性。机制研究表明，硝基芳烃形成碱活化的n -甲基吡咯烷酮结合加合物，产生类似苯胺的中间体，与酰基钯配合物偶联，以提供所需的酰胺。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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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.