nhc催化合成硼立体原体dipys的动力学拆分

IF 11.3 1区化学 Q1 CHEMISTRY, PHYSICAL

ACS Catalysis Pub Date : 2025-05-16 DOI:10.1021/acscatal.5c01629

Yuan-Yuan Gao, Yu-Jing Liang, Gaowei Li, Lu Li, Zhi-Yuan Hu, Wen-Hao Lin, Xue-Hui Huang, Yu Chen, Xuzhao Du, Peiyuan Yu, Qiuling Song, Lantao Liu

{"title":"nhc催化合成硼立体原体dipys的动力学拆分","authors":"Yuan-Yuan Gao, Yu-Jing Liang, Gaowei Li, Lu Li, Zhi-Yuan Hu, Wen-Hao Lin, Xue-Hui Huang, Yu Chen, Xuzhao Du, Peiyuan Yu, Qiuling Song, Lantao Liu","doi":"10.1021/acscatal.5c01629","DOIUrl":null,"url":null,"abstract":"The enantioselective synthesis of boron-stereogenic compounds remains a formidable challenge in modern synthetic chemistry due to the limited availability of efficient catalytic strategies. Herein, we report an N-heterocyclic carbene (NHC)-catalyzed kinetic resolution of 3-formyl BODIPYs, which provides access to enantioenriched 3-formyl BODIPYs and aryl 3-carboxylate BODIPYs in good to high yields with high enantioselectivities (up to 96% ee). This method features a broad substrate scope, mild reaction conditions, and exceptional functional group tolerance. Furthermore, the resulting chiral BODIPYs exhibit promising circularly polarized luminescence properties. This work represents the successful application of NHC catalysis for constructing boron-stereogenic centers, expanding the toolbox for asymmetric organocatalysis.","PeriodicalId":9,"journal":{"name":"ACS Catalysis ","volume":"30 1","pages":""},"PeriodicalIF":11.3000,"publicationDate":"2025-05-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"NHC-Catalyzed Kinetic Resolution for the Synthesis of Boron-Stereogenic BODIPYs\",\"authors\":\"Yuan-Yuan Gao, Yu-Jing Liang, Gaowei Li, Lu Li, Zhi-Yuan Hu, Wen-Hao Lin, Xue-Hui Huang, Yu Chen, Xuzhao Du, Peiyuan Yu, Qiuling Song, Lantao Liu\",\"doi\":\"10.1021/acscatal.5c01629\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"The enantioselective synthesis of boron-stereogenic compounds remains a formidable challenge in modern synthetic chemistry due to the limited availability of efficient catalytic strategies. Herein, we report an N-heterocyclic carbene (NHC)-catalyzed kinetic resolution of 3-formyl BODIPYs, which provides access to enantioenriched 3-formyl BODIPYs and aryl 3-carboxylate BODIPYs in good to high yields with high enantioselectivities (up to 96% ee). This method features a broad substrate scope, mild reaction conditions, and exceptional functional group tolerance. Furthermore, the resulting chiral BODIPYs exhibit promising circularly polarized luminescence properties. This work represents the successful application of NHC catalysis for constructing boron-stereogenic centers, expanding the toolbox for asymmetric organocatalysis.\",\"PeriodicalId\":9,\"journal\":{\"name\":\"ACS Catalysis \",\"volume\":\"30 1\",\"pages\":\"\"},\"PeriodicalIF\":11.3000,\"publicationDate\":\"2025-05-16\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"ACS Catalysis \",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1021/acscatal.5c01629\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, PHYSICAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"ACS Catalysis ","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acscatal.5c01629","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}

引用次数: 0

摘要

由于有效的催化策略有限，硼立体化合物的对映选择性合成仍然是现代合成化学中的一个巨大挑战。在此，我们报道了一个n -杂环羰基（NHC）催化的3-甲酰基BODIPYs的动力学分解，它提供了对映富集的3-甲酰基BODIPYs和芳基3-羧酸BODIPYs的高收率和高对映选择性（高达96% ee）。该方法具有底物范围广，反应条件温和，功能基团耐受性好等特点。此外，所得的手性BODIPYs具有良好的圆偏振发光特性。这项工作代表了NHC催化在构建硼立体中心中的成功应用，扩展了不对称有机催化的工具箱。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

NHC-Catalyzed Kinetic Resolution for the Synthesis of Boron-Stereogenic BODIPYs

查看原文本刊更多论文

NHC-Catalyzed Kinetic Resolution for the Synthesis of Boron-Stereogenic BODIPYs

The enantioselective synthesis of boron-stereogenic compounds remains a formidable challenge in modern synthetic chemistry due to the limited availability of efficient catalytic strategies. Herein, we report an N-heterocyclic carbene (NHC)-catalyzed kinetic resolution of 3-formyl BODIPYs, which provides access to enantioenriched 3-formyl BODIPYs and aryl 3-carboxylate BODIPYs in good to high yields with high enantioselectivities (up to 96% ee). This method features a broad substrate scope, mild reaction conditions, and exceptional functional group tolerance. Furthermore, the resulting chiral BODIPYs exhibit promising circularly polarized luminescence properties. This work represents the successful application of NHC catalysis for constructing boron-stereogenic centers, expanding the toolbox for asymmetric organocatalysis.

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

ACS Catalysis CHEMISTRY, PHYSICAL-

CiteScore

20.80

自引率

6.20%

发文量

1253

审稿时长

1.5 months

期刊介绍： ACS Catalysis is an esteemed journal that publishes original research in the fields of heterogeneous catalysis, molecular catalysis, and biocatalysis. It offers broad coverage across diverse areas such as life sciences, organometallics and synthesis, photochemistry and electrochemistry, drug discovery and synthesis, materials science, environmental protection, polymer discovery and synthesis, and energy and fuels. The scope of the journal is to showcase innovative work in various aspects of catalysis. This includes new reactions and novel synthetic approaches utilizing known catalysts, the discovery or modification of new catalysts, elucidation of catalytic mechanisms through cutting-edge investigations, practical enhancements of existing processes, as well as conceptual advances in the field. Contributions to ACS Catalysis can encompass both experimental and theoretical research focused on catalytic molecules, macromolecules, and materials that exhibit catalytic turnover.