{"title":"以能量转移或单电子转移引发双环[1.1.0]丁烷与（苯并）呋喃和（苯并）噻吩的分子内脱芳[2π + 2σ]光环加成反应","authors":"Yuyue Li, Xintao Gu, Yin Wei, Min Shi","doi":"10.1007/s11426-025-2704-x","DOIUrl":null,"url":null,"abstract":"<div><p>Dearomative photocycloaddition of heteroarenes is an efficient method for replacing planar arenes with three-dimensional (3D) scaffolds, such as bicyclo[2.1.1]-hexane (BCH) containing heterocycles. Herein, we report intramolecular dearomative [2π + 2σ] photocycloadditions of bicyclo[1.1.0]butanes (BCBs) with (benzo)furans and (benzo)thiophenes. These photocycloadditions are initiated through an energy transfer pathway (EnT) or single electron transfer pathway (SET), efficiently yielding unique BCH-pyrrolidinone-fused heterocyclic scaffolds. Moreover, the synthetic utility of this photochemical reaction was demonstrated on the basis of large-scale synthesis and diversified transformations. Mechanistic investigations, in conjunction with density functional theory (DFT) calculations, were taken to support the proposed reaction mechanisms.\n</p><div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":772,"journal":{"name":"Science China Chemistry","volume":"68 10","pages":"4959 - 4972"},"PeriodicalIF":9.7000,"publicationDate":"2025-06-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Intramolecular dearomative [2π + 2σ] photocycloadditions of bicyclo[1.1.0]butanes with (benzo)furans and (benzo)thiophenes initiated by energy transfer or single electron transfer\",\"authors\":\"Yuyue Li, Xintao Gu, Yin Wei, Min Shi\",\"doi\":\"10.1007/s11426-025-2704-x\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Dearomative photocycloaddition of heteroarenes is an efficient method for replacing planar arenes with three-dimensional (3D) scaffolds, such as bicyclo[2.1.1]-hexane (BCH) containing heterocycles. Herein, we report intramolecular dearomative [2π + 2σ] photocycloadditions of bicyclo[1.1.0]butanes (BCBs) with (benzo)furans and (benzo)thiophenes. These photocycloadditions are initiated through an energy transfer pathway (EnT) or single electron transfer pathway (SET), efficiently yielding unique BCH-pyrrolidinone-fused heterocyclic scaffolds. Moreover, the synthetic utility of this photochemical reaction was demonstrated on the basis of large-scale synthesis and diversified transformations. Mechanistic investigations, in conjunction with density functional theory (DFT) calculations, were taken to support the proposed reaction mechanisms.\\n</p><div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>\",\"PeriodicalId\":772,\"journal\":{\"name\":\"Science China Chemistry\",\"volume\":\"68 10\",\"pages\":\"4959 - 4972\"},\"PeriodicalIF\":9.7000,\"publicationDate\":\"2025-06-23\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Science China Chemistry\",\"FirstCategoryId\":\"1\",\"ListUrlMain\":\"https://link.springer.com/article/10.1007/s11426-025-2704-x\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Science China Chemistry","FirstCategoryId":"1","ListUrlMain":"https://link.springer.com/article/10.1007/s11426-025-2704-x","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Intramolecular dearomative [2π + 2σ] photocycloadditions of bicyclo[1.1.0]butanes with (benzo)furans and (benzo)thiophenes initiated by energy transfer or single electron transfer
Dearomative photocycloaddition of heteroarenes is an efficient method for replacing planar arenes with three-dimensional (3D) scaffolds, such as bicyclo[2.1.1]-hexane (BCH) containing heterocycles. Herein, we report intramolecular dearomative [2π + 2σ] photocycloadditions of bicyclo[1.1.0]butanes (BCBs) with (benzo)furans and (benzo)thiophenes. These photocycloadditions are initiated through an energy transfer pathway (EnT) or single electron transfer pathway (SET), efficiently yielding unique BCH-pyrrolidinone-fused heterocyclic scaffolds. Moreover, the synthetic utility of this photochemical reaction was demonstrated on the basis of large-scale synthesis and diversified transformations. Mechanistic investigations, in conjunction with density functional theory (DFT) calculations, were taken to support the proposed reaction mechanisms.
期刊介绍：
Science China Chemistry, co-sponsored by the Chinese Academy of Sciences and the National Natural Science Foundation of China and published by Science China Press, publishes high-quality original research in both basic and applied chemistry. Indexed by Science Citation Index, it is a premier academic journal in the field.
Categories of articles include:
Highlights. Brief summaries and scholarly comments on recent research achievements in any field of chemistry.
Perspectives. Concise reports on thelatest chemistry trends of interest to scientists worldwide, including discussions of research breakthroughs and interpretations of important science and funding policies.
Reviews. In-depth summaries of representative results and achievements of the past 5–10 years in selected topics based on or closely related to the research expertise of the authors, providing a thorough assessment of the significance, current status, and future research directions of the field.
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