通过能量转移使 2-乙烯氧基芳基炔与溴丙二酸盐发生光化学[2 + 2 + 1]环化反应

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2024-04-16 DOI:10.1039/D4QO00249K

Shuo Tang, Jiupeng Liu, Min Zhang, Dan Wang, Yong Wang, Jingjing Zhao and Pan Li

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引用次数: 0

摘要

我们开发了一种 2-乙烯氧基芳基炔与溴丙二酸盐的光化学[2 + 2 + 1]自由基环化反应。该方案提供了一种在温和条件下制备环戊并[b]苯并呋喃的无金属、无光催化剂、无氧化剂和无碱的方法。这一串联反应包括连续的自由基加成、5-外-二元环化、1,5-H 变换、5-内-三元环化、自由基偶联和消除过程。值得注意的是，光诱导的溴马隆酸酯 C-Br 键均裂会发生能量转移，而溶剂 DMF 则是一种酸结合试剂。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Photochemical [2 + 2 + 1] annulation of 2-vinyloxy arylalkynes with bromomalonates via energy transfer†

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Photochemical [2 + 2 + 1] annulation of 2-vinyloxy arylalkynes with bromomalonates via energy transfer†

A photochemical [2 + 2 + 1] radical annulation of 2-vinyloxy arylalkynes with bromomalonates has been developed. This protocol affords a transition-metal-free, oxidant-free and base-free approach to cyclopenta[b]benzofurans under mild conditions. This tandem reaction involves sequential radical addition, 5-exo-dig cyclization, 1,5-H shift, 5-endo-trig annulation, radical coupling, and elimination processes. Significantly, the photoinduced C–Br bond homolysis of bromomalonates involves an energy transfer, and the solvent DMF acts as an acid-binding reagent.

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来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.