{"title":"Intramolecular Crossed [2 + 2] Cycloaddition through Visible-light Triplet Sensitization: Expedient Access to Bridged Bicyclic Alkene","authors":"Min Li, Le-Yi Tao, Xin-Tao Gu, Yin Wei, Min Shi","doi":"10.1002/adsc.202401402","DOIUrl":null,"url":null,"abstract":"A visible-light-induced intramolecular crossed [2 + 2] cycloaddition reaction of allene-tethered alkylidenecyclopropanes was reported in this paper. The reactions were conducted under mild conditions using Iridium(III) catalyst FirPic as a photosensitizer for energy transfer, affording bridged bicyclic alkenes in moderate to good yields with excellent regioselectivity and stereoselectivity through the regulation of substituents at the olefin’s terminal position. Meanwhile, the computational study explained the special region control assisted by sulfonyl radicals in detail.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"84 1","pages":""},"PeriodicalIF":4.4000,"publicationDate":"2025-01-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Advanced Synthesis & Catalysis","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/adsc.202401402","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
引用次数: 0
Abstract
A visible-light-induced intramolecular crossed [2 + 2] cycloaddition reaction of allene-tethered alkylidenecyclopropanes was reported in this paper. The reactions were conducted under mild conditions using Iridium(III) catalyst FirPic as a photosensitizer for energy transfer, affording bridged bicyclic alkenes in moderate to good yields with excellent regioselectivity and stereoselectivity through the regulation of substituents at the olefin’s terminal position. Meanwhile, the computational study explained the special region control assisted by sulfonyl radicals in detail.
期刊介绍：
Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry.
The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.
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