{"title":"元-二取代[n]对位环烷的高对映选择性合成方法","authors":"Jia Li, Ziyang Dong, Hongxuan Zhai, Jicheng Wu, Changgui Zhao","doi":"10.1021/acs.joc.4c02021","DOIUrl":null,"url":null,"abstract":"Atroposelective synthesis of <i>meta</i>-disubstituted [<i>n</i>]paracyclophanes is a difficult task in organic chemistry. We describe a facile approach for the synthesis of <i>meta</i>-disubstituted [<i>n</i>]paracyclophanes using Pd-catalyzed enantioselective C–H olefination and sequential reductive cleavage. A wide range of [<i>n</i>]paracyclophanes was obtained with excellent enantioselectivity. Thermodynamic analysis revealed that the rotational barrier of <i>meta</i>-disubstituted [<i>n</i>]paracyclophanes was lower than that of <i>para</i>-disubstituted [<i>n</i>]paracyclophanes. The synthesized planar-chiral [14]paracyclophane showed a bright fluorescence emission and impressive circularly polarized luminescence activity.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3000,"publicationDate":"2024-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"An Approach for Highly Enantioselective Synthesis of meta-Disubstituted [n]Paracyclophanes\",\"authors\":\"Jia Li, Ziyang Dong, Hongxuan Zhai, Jicheng Wu, Changgui Zhao\",\"doi\":\"10.1021/acs.joc.4c02021\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Atroposelective synthesis of <i>meta</i>-disubstituted [<i>n</i>]paracyclophanes is a difficult task in organic chemistry. We describe a facile approach for the synthesis of <i>meta</i>-disubstituted [<i>n</i>]paracyclophanes using Pd-catalyzed enantioselective C–H olefination and sequential reductive cleavage. A wide range of [<i>n</i>]paracyclophanes was obtained with excellent enantioselectivity. Thermodynamic analysis revealed that the rotational barrier of <i>meta</i>-disubstituted [<i>n</i>]paracyclophanes was lower than that of <i>para</i>-disubstituted [<i>n</i>]paracyclophanes. The synthesized planar-chiral [14]paracyclophane showed a bright fluorescence emission and impressive circularly polarized luminescence activity.\",\"PeriodicalId\":57,\"journal\":{\"name\":\"The Journal of Organic Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":3.3000,\"publicationDate\":\"2024-09-27\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"The Journal of Organic Chemistry\",\"FirstCategoryId\":\"1\",\"ListUrlMain\":\"https://doi.org/10.1021/acs.joc.4c02021\",\"RegionNum\":2,\"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":"The Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c02021","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
An Approach for Highly Enantioselective Synthesis of meta-Disubstituted [n]Paracyclophanes
Atroposelective synthesis of meta-disubstituted [n]paracyclophanes is a difficult task in organic chemistry. We describe a facile approach for the synthesis of meta-disubstituted [n]paracyclophanes using Pd-catalyzed enantioselective C–H olefination and sequential reductive cleavage. A wide range of [n]paracyclophanes was obtained with excellent enantioselectivity. Thermodynamic analysis revealed that the rotational barrier of meta-disubstituted [n]paracyclophanes was lower than that of para-disubstituted [n]paracyclophanes. The synthesized planar-chiral [14]paracyclophane showed a bright fluorescence emission and impressive circularly polarized luminescence activity.
期刊介绍：
The Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
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