铜介导的三组分合成各种全氟烷基化富勒烯

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-01-28 DOI:10.1021/acs.joc.4c0275310.1021/acs.joc.4c02753

Si-Si Liang, Qian Zhou, Pei-Xi Wu, Xiao-Man Huang, Meng-Ping Shu, Xiao-Ming Zhu, Liang Xu* and Guan-Wu Wang*,

{"title":"铜介导的三组分合成各种全氟烷基化富勒烯","authors":"Si-Si Liang, Qian Zhou, Pei-Xi Wu, Xiao-Man Huang, Meng-Ping Shu, Xiao-Ming Zhu, Liang Xu* and Guan-Wu Wang*, ","doi":"10.1021/acs.joc.4c0275310.1021/acs.joc.4c02753","DOIUrl":null,"url":null,"abstract":"The synthesis of perfluoroalkylated fullerenes (PFAFs) holds significant importance due to their enhanced molecular stability, increased lipophilicity, and high electron affinity. Herein, we report a copper-catalyzed multicomponent reaction conducted under aerobic conditions, which enables the production of highly soluble PFAFs with half-wave reduction potentials similar to those of C60. Furthermore, the challenges posed by C–F coupling in carbon signal assignment were addressed through fluorine-decoupled carbon spectroscopy, facilitating precise structural characterization of the perfluoroalkyl moieties.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 5","pages":"2022–2035 2022–2035"},"PeriodicalIF":3.6000,"publicationDate":"2025-01-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Copper-Mediated Three-Component Synthesis of Diverse Perfluoroalkylated Fullerenes\",\"authors\":\"Si-Si Liang, Qian Zhou, Pei-Xi Wu, Xiao-Man Huang, Meng-Ping Shu, Xiao-Ming Zhu, Liang Xu* and Guan-Wu Wang*, \",\"doi\":\"10.1021/acs.joc.4c0275310.1021/acs.joc.4c02753\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"The synthesis of perfluoroalkylated fullerenes (PFAFs) holds significant importance due to their enhanced molecular stability, increased lipophilicity, and high electron affinity. Herein, we report a copper-catalyzed multicomponent reaction conducted under aerobic conditions, which enables the production of highly soluble PFAFs with half-wave reduction potentials similar to those of C60. Furthermore, the challenges posed by C–F coupling in carbon signal assignment were addressed through fluorine-decoupled carbon spectroscopy, facilitating precise structural characterization of the perfluoroalkyl moieties.\",\"PeriodicalId\":57,\"journal\":{\"name\":\"Journal of Organic Chemistry\",\"volume\":\"90 5\",\"pages\":\"2022–2035 2022–2035\"},\"PeriodicalIF\":3.6000,\"publicationDate\":\"2025-01-28\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Organic Chemistry\",\"FirstCategoryId\":\"1\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acs.joc.4c02753\",\"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":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.joc.4c02753","RegionNum":2,"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

全氟烷基化富勒烯（PFAFs）的合成具有重要意义，因为它们具有增强的分子稳定性，增加的亲脂性和高电子亲和力。在此，我们报道了在好氧条件下进行的铜催化多组分反应，该反应可以生产具有与C60相似的半波还原电位的高可溶性pafs。此外，通过氟解耦碳光谱解决了碳信号分配中C-F耦合带来的挑战，促进了全氟烷基部分的精确结构表征。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Copper-Mediated Three-Component Synthesis of Diverse Perfluoroalkylated Fullerenes

查看原文本刊更多论文

Copper-Mediated Three-Component Synthesis of Diverse Perfluoroalkylated Fullerenes

The synthesis of perfluoroalkylated fullerenes (PFAFs) holds significant importance due to their enhanced molecular stability, increased lipophilicity, and high electron affinity. Herein, we report a copper-catalyzed multicomponent reaction conducted under aerobic conditions, which enables the production of highly soluble PFAFs with half-wave reduction potentials similar to those of C₆₀. Furthermore, the challenges posed by C–F coupling in carbon signal assignment were addressed through fluorine-decoupled carbon spectroscopy, facilitating precise structural characterization of the perfluoroalkyl moieties.

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

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： 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.