Organic Photoredox Catalytic Difluoroalkylation of Unactivated Olefins to Access Difluoro-Containing Tetrahydropyridazines

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-11-14 DOI:10.1021/acs.orglett.4c03829

Jun Sun, Yu Wei, Ting Lv, Chaodong Wang, Shengjie Song, Jiadi Zhou, Jianjun Li

引用次数: 0

Abstract

Herein, we disclose a readily available phenothiazine derivative as an organocatalyst, which upon excitation with 371 nm light acquires a strongly reducing power and serves to induce the radical cascade difluoromethylation/cyclization reaction of N-homoallylacetohydrazides. A variety of CF₂COR-tetrahydropyridazines have been obtained in moderate to excellent yields. This catalytic platform proceeds under metal-free conditions with a wide substrate scope and broad functional group compatibility, which unlocks the new reactivity of phenothiazine derivatives and adds significant synthetic value to N-heterocycles.

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有机光氧化催化未活化烯烃的二氟烷基化反应以获得含二氟的四氢哒嗪

在此，我们揭示了一种易于获得的吩噻嗪衍生物作为有机催化剂，它在 371 纳米光的激发下获得强还原力，并可诱导 N-高烯丙基乙酰肼的自由基级联二氟甲基化/环化反应。我们以中等到极好的收率获得了多种 CF2COR-四氢哒嗪。该催化平台在无金属条件下进行，具有广泛的底物范围和宽泛的官能团兼容性，从而释放了吩噻嗪衍生物的新反应活性，并为 N-杂环增加了重要的合成价值。

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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.