Metal-Free Visible-Light Excitation of TMSN3 Enables [3 + 2] Cycloaddition of Arylidenecyclopropanes with Olefins

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-04-14 DOI:10.1021/acs.orglett.5c0033510.1021/acs.orglett.5c00335

Ya-Yu Wang, Ting-Feng Fu, Xiao Hu, Bo Liu, Ming-Yu Teng, Guo-Li Huang* and Lei Zhang*,

引用次数: 0

Abstract

A visible-light photoredox [3 + 2] cycloaddition reaction of arylidenecyclopropanes with olefins was developed, employing the readily available and commercially accessible TMSN₃ as an efficient radical mediator. This method provides a convenient and efficient route to arylidenecyclopentanes from readily available starting materials, is metal-free, and features enhanced atom and step economy, excellent selectivity, extensive substrate versatility, favorable functional group compatibility, structural diversity, and mild reaction conditions, which further enable late-stage diversification. DFT calculations elucidated that this transformation entails sequential radical generation, radical addition, ring-opening, radical cyclization, and elimination steps.

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TMSN3的无金属可见光激发实现了芳基环丙烷与烯烃的[3 + 2]环加成反应

摘要以易得的TMSN3作为有效的自由基介质，研究了芳基环丙烷与烯烃的可见光光氧化还原[3 + 2]环加成反应。该方法为从现成的原料制备芳基环戊烷提供了一条便捷、高效的途径，不含金属，具有原子经济性和步骤经济性强、选择性好、底物通用性强、官能团相容性好、结构多样性好、反应条件温和等特点，进一步促进了后期多样化。DFT计算表明，这种转变需要连续的自由基生成、自由基相加、开环、自由基环化和消除步骤。

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.