Photoredox Nickel-Catalyzed Coupling/Controllable Defluorination: Access to α-Fluoroarylacetic Amides and Acetates

IF 5 1区 化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-03-12 DOI:10.1021/acs.orglett.5c00526
Jie Gao, Pin-Pin Yao, Xian-Chen He, Zhi-Peng Ye, Yan-Ling Liu, Hao-Yue Xiang, Kai Chen, Hua Yang
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Abstract

Herein, an electron donor–acceptor complex (EDA)-enabled photoredox nickel-catalyzed coupling/controllable defluorination domino sequence has been successfully developed, providing an efficient route to a series of α-fluoroarylacetic esters and amides. This methodology accommodates a diverse array of commercially available aryl bromides and chlorodifluoroaryl carboxylic acid derivatives as suitable substrates. Preliminary mechanistic investigations suggest that the reaction is initiated by photoinduced EDA-enabled/nickel-catalyzed direct cross-electrophile coupling, with further defluorination proceeding through the generation of EDA complexes, facilitating a controllable reductive defluorination process.

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光氧化还原镍催化偶联/可控脱氟:获得α-氟芳基乙酸酰胺和乙酸酯
本文成功开发了一种电子给受体配合物(EDA)激活的光氧化还原镍催化偶联/可控脱氟多米诺骨牌序列,为一系列α-氟芳基乙酸酯和酰胺提供了一条有效的途径。该方法适用于各种各样的市售芳基溴和氯二氟芳基羧酸衍生物作为合适的底物。初步的机理研究表明,该反应是由光诱导的EDA激活/镍催化的直接交叉亲电偶联引发的,通过生成EDA配合物进一步脱氟,促进了可控的还原性脱氟过程。
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来源期刊
Organic Letters
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.
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