Organophotoredox Dioxygenation of Alkenes via ROH···F-Activated N-Alkoxyphthalimides.

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-09-30 DOI:10.1021/acs.orglett.5c03734

Pau Sarró,Albert Gallego-Gamo,Elies Molins,Roser Pleixats,Carolina Gimbert-Suriñach,Adelina Vallribera,Albert Granados

引用次数: 0

Abstract

The generation and controlled reactivity of alkoxyl radicals remain challenging due to their high energy and tendency for β-scission or hydrogen atom transfer events. Herein, we report a photoredox-catalyzed dioxygenation of alkenes enabled by the activation of fluorinated N-alkoxyphthalimides through hydrogen-bonded aggregates with ROH···F. This transformation proceeds under mild, metal-free conditions using an organophotocatalyst and a simple alcohol, affording a diverse range of dialkoxylated products with high functional group tolerance and good scalability. Mechanistic studies─including UV-Vis spectroscopy, NMR, cyclic voltammetry, and Stern-Volmer quenching─reveal a radical/polar crossover pathway.

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通过ROH··f活化的n -烷氧基邻苯二胺进行烯烃的有机光氧化还原双氧合。

由于烷氧基自由基能量高，易于发生β-断裂或氢原子转移事件，其生成和控制反应活性仍然具有挑战性。本文报道了一种光氧化催化的烯烃双氧化反应，该反应是通过与ROH···F的氢键聚集体激活氟化n-烷氧基酞酰亚胺实现的。这种转化在温和的、无金属的条件下进行，使用有机光催化剂和简单的醇，提供多种具有高官能团耐受性和良好可扩展性的二氧基化产物。机理研究──包括紫外-可见光谱、核磁共振、循环伏安法和斯特恩-沃尔默猝灭──揭示了自由基/极性交叉途径。

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.