Photocatalyzed/Base-Mediated Defluorinative Three-Component Cascade Cyclization: Access to Monofluorocyclohexenes and 6-Fluoro-1,2,3,4-tetrahydropyridines

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-03-19 DOI:10.1021/acs.orglett.5c00675

Shuyue Zhang, Meixue Gan, Fan Zhang, Lei Zhou, Weiyu Li

引用次数: 0

Abstract

A three-component cascade cyclization of α-CF₃ alkenes, electron-rich alkenes, and dimethyl esters or sulfonamides via a dual C–F bond cleavage process is described. This methodology provides a general and efficient strategy to access monofluorocyclohexenes and 6-fluoro-1,2,3,4-tetrahydropyridines by switching the bifunctional reagents (dimethyl esters or sulfonamides), which are valuable building blocks in synthetic chemistry and the pharmaceutical industries. The reaction mechanism and the synthetic applications of the products have been demonstrated.

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光催化/碱介导的脱氟三组分级联环化：获得单氟环己烯和6-氟-1,2,3,4-四氢吡啶

通过双C-F键裂解，描述了α-CF3烯烃、富电子烯烃和二甲酯或磺胺类化合物的三组分级联环化反应。该方法通过转换双功能试剂（二甲酯或磺胺类），提供了一种获取单氟环己烯和6-氟-1,2,3,4-四氢吡啶的通用和有效策略，这些试剂是合成化学和制药工业中宝贵的组成部分。介绍了反应机理和产物的合成应用。

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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.