Haijian Wu , Manman Sun , Jing Zhang , Zhiming Wang , Jianguo Yang , Gangguo Zhu
{"title":"hfip促进对醌类化合物与双环[1.1.0]丁烷的形式[2π + 2σ]环加成反应：与螺环-双环[2.1.1]己烷的近似","authors":"Haijian Wu , Manman Sun , Jing Zhang , Zhiming Wang , Jianguo Yang , Gangguo Zhu","doi":"10.1039/d4qo02226b","DOIUrl":null,"url":null,"abstract":"<div><div>A formal [2π + 2σ] cycloaddition of BCBs with <em>p</em>-QMs has been developed using a small amount of HFIP (2 M) as the solvent without an additional catalyst, in which HFIP also served as a H-bond donor and a cationic stabilizer. This protocol enables the rapid construction of spiro-BCHs in good to excellent yields with a broad substrate scope. Easy scale-up synthesis, potential applications in the modification of bioactive products, mild reaction conditions and simple operation are its practical advantages.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 6","pages":"Pages 1951-1957"},"PeriodicalIF":0.0000,"publicationDate":"2025-01-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"HFIP-promoted formal [2π + 2σ] cycloaddition of para-quinone methides with bicyclo[1.1.0]butanes: an approach towards spiro-bicyclo[2.1.1]hexanes†\",\"authors\":\"Haijian Wu , Manman Sun , Jing Zhang , Zhiming Wang , Jianguo Yang , Gangguo Zhu\",\"doi\":\"10.1039/d4qo02226b\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>A formal [2π + 2σ] cycloaddition of BCBs with <em>p</em>-QMs has been developed using a small amount of HFIP (2 M) as the solvent without an additional catalyst, in which HFIP also served as a H-bond donor and a cationic stabilizer. This protocol enables the rapid construction of spiro-BCHs in good to excellent yields with a broad substrate scope. Easy scale-up synthesis, potential applications in the modification of bioactive products, mild reaction conditions and simple operation are its practical advantages.</div></div>\",\"PeriodicalId\":94379,\"journal\":{\"name\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"volume\":\"12 6\",\"pages\":\"Pages 1951-1957\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2025-01-22\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S2052412925000269\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic chemistry frontiers : an international journal of organic chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S2052412925000269","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
HFIP-promoted formal [2π + 2σ] cycloaddition of para-quinone methides with bicyclo[1.1.0]butanes: an approach towards spiro-bicyclo[2.1.1]hexanes†
A formal [2π + 2σ] cycloaddition of BCBs with p-QMs has been developed using a small amount of HFIP (2 M) as the solvent without an additional catalyst, in which HFIP also served as a H-bond donor and a cationic stabilizer. This protocol enables the rapid construction of spiro-BCHs in good to excellent yields with a broad substrate scope. Easy scale-up synthesis, potential applications in the modification of bioactive products, mild reaction conditions and simple operation are its practical advantages.
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