A Photo- and Electrochemistry-Triggered Redox-Neutral Cyclization Strategy to Access Cyclic N-CF3 Amides

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-03-14 DOI:10.1021/acs.orglett.5c0035510.1021/acs.orglett.5c00355

Abdurrahman Turksoy, Andrea Weßels, Kristina Deckers, Christian D.-T. Nielsen and Franziska Schoenebeck*,

引用次数: 0

Abstract

While the construction of N-CF₃ amides has seen significant progress, the current synthetic repertoire is largely limited to noncyclic variants. Here, we report synthetic access to N-CF₃ isoindolinones. The developed redox-neutral cyclization leverages amino acid-derived N-CF₃ redox-active esters under photo- or electrochemical activation. Mechanistic studies reveal that N-CF₃ uniquely enables this disconnection through its distinct electronic impact, which enhances conformational flexibility and lowers the propensity for overoxidation.

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光电化学触发氧化还原-中性环化策略以获得环N-CF3酰胺

虽然N-CF3酰胺的构建取得了重大进展，但目前的合成曲目主要限于非环变体。在这里，我们报道了N-CF3异吲哚酮的合成途径。开发的氧化还原中性环化利用氨基酸衍生的N-CF3氧化还原活性酯在光或电化学活化下。机制研究表明，N-CF3通过其独特的电子冲击独特地实现了这种断开，从而增强了构象灵活性并降低了过度氧化的倾向。

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.