Practical heptafluoroisopropylation of nitrogen-containing (hetero)aromatics under visible light

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2024-11-26 DOI:10.1039/d4qo01660b

Xin Luo, Shao-Jie Lou, Yan-Biao Sun, Cheng-Cheng Jing, Xiang Fei, Xiaoxiao Zhang, Jing-Jing Zhai, Yifeng Wang, Dan-Qian Xu

引用次数: 0

Abstract

A practical visible-light-driven heptafluoroisopropylation of substituted anilines and heterocyclic aromatics has been achieved. The key to the success of this facile transformation lies in the in-situ generation of a novel electron donor-acceptor (EDA) complex between trimethyl phosphite and heptafluoroisopropyl iodide, which enables the formation of diverse heptafluoroisopropylated products in a regio-selective fashion under mild reaction conditions. In addition, the present EDA protocol demonstrates applicability for other perfluoroalkylation reactions. This work features high site-selectivity, transition-metal and photosensitizer free conditions, and broad substrate scope, constituting a greener alternative to access the synthetically important perfluoroalkyl-containing molecules, such as Broflanilide.

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可见光下含氮（杂）芳烃的实用七氟异丙化反应

我们实现了一种实用的可见光驱动的取代苯胺和杂环芳烃的七氟异丙基化反应。这种简便转化成功的关键在于在亚磷酸三甲酯和七氟异丙基碘化物之间原位生成了一种新型电子供体-受体（EDA）复合物，从而能够在温和的反应条件下以区域选择性的方式形成多种七氟异丙基化产物。此外，本 EDA 方案还适用于其他全氟烷基化反应。这项工作具有高位点选择性、不含过渡金属和光敏剂的条件以及广泛的底物范围等特点，是获得重要的全氟烷基分子（如 Broflanilide）的绿色替代方法。

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 Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.