可见光激发路易斯酸催化分子间[2σ + 3π]光环加成。

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-09-30 DOI:10.1021/acs.orglett.5c03637

Tianlei Du,Yunzhi Xie,Qiujie Qin,Kun Yin,Jian Li,Xinyao Li,Zijun Zhou

{"title":"可见光激发路易斯酸催化分子间[2σ + 3π]光环加成。","authors":"Tianlei Du,Yunzhi Xie,Qiujie Qin,Kun Yin,Jian Li,Xinyao Li,Zijun Zhou","doi":"10.1021/acs.orglett.5c03637","DOIUrl":null,"url":null,"abstract":"Herein, we introduce an innovative approach employing a direct visible-light-excited Lewis acid-catalyzed [2σ + 3π] cycloaddition reaction between bicyclo[1.1.0]butanes and α-vinyl azides via diradical intermediate. This transformation proceeds efficiently in the absence of any external photocatalyst produces versatile 2-azabicyclo[3.1.1]heptene derivatives with a broad substrate scope, achieving yields of up to 94% across 34 examples. The synthetic practicality was further demonstrated through a scaled-up reaction, and the transformation of the imidazole auxiliary into an ester group.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"18 1","pages":""},"PeriodicalIF":5.0000,"publicationDate":"2025-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Visible-Light-Excited Lewis Acid Catalyzed Intermolecular [2σ + 3π] Photocycloadditions.\",\"authors\":\"Tianlei Du,Yunzhi Xie,Qiujie Qin,Kun Yin,Jian Li,Xinyao Li,Zijun Zhou\",\"doi\":\"10.1021/acs.orglett.5c03637\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Herein, we introduce an innovative approach employing a direct visible-light-excited Lewis acid-catalyzed [2σ + 3π] cycloaddition reaction between bicyclo[1.1.0]butanes and α-vinyl azides via diradical intermediate. This transformation proceeds efficiently in the absence of any external photocatalyst produces versatile 2-azabicyclo[3.1.1]heptene derivatives with a broad substrate scope, achieving yields of up to 94% across 34 examples. The synthetic practicality was further demonstrated through a scaled-up reaction, and the transformation of the imidazole auxiliary into an ester group.\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":\"18 1\",\"pages\":\"\"},\"PeriodicalIF\":5.0000,\"publicationDate\":\"2025-09-30\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1021/acs.orglett.5c03637\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.5c03637","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

摘要

本文介绍了一种创新的方法，利用直接可见光激发路易斯酸催化的[2σ + 3π]环加成反应，在双环[1.1.0]丁烷和α-乙烯基叠氮化物之间通过双自由基中间体进行。在没有任何外部光催化剂的情况下，这种转化有效地进行，产生了具有广泛底物范围的通用2-氮杂环[3.1.1]庚烯衍生物，在34个例子中，产率高达94%。通过放大反应，并将咪唑助剂转化为酯基，进一步证明了合成的实用性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

查看原文本刊更多论文

Visible-Light-Excited Lewis Acid Catalyzed Intermolecular [2σ + 3π] Photocycloadditions.

Herein, we introduce an innovative approach employing a direct visible-light-excited Lewis acid-catalyzed [2σ + 3π] cycloaddition reaction between bicyclo[1.1.0]butanes and α-vinyl azides via diradical intermediate. This transformation proceeds efficiently in the absence of any external photocatalyst produces versatile 2-azabicyclo[3.1.1]heptene derivatives with a broad substrate scope, achieving yields of up to 94% across 34 examples. The synthetic practicality was further demonstrated through a scaled-up reaction, and the transformation of the imidazole auxiliary into an ester group.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

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.