Enantioselective construction of inherently chiral pillar[5]arenes via palladium-catalysed Suzuki–Miyaura cross-coupling
Abstract Pillar[n]arenes have broad applications in biological medicine, materials science, and supramolecular gels. Notably, enantiopure pillar[5]arenes are valued for their roles in enantioselective host–guest recognition, chiral sensing, asymmetric catalysis, and related fields. Current methods f...
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2025-03-01
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| Series: | Nature Communications |
| Online Access: | https://doi.org/10.1038/s41467-025-57461-x |
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| author | Ting-Rui Luan Che Sun Yong-Le Tian Yu-Kun Jiang Long-Long Xi Ren-Rong Liu |
| author_facet | Ting-Rui Luan Che Sun Yong-Le Tian Yu-Kun Jiang Long-Long Xi Ren-Rong Liu |
| author_sort | Ting-Rui Luan |
| collection | DOAJ |
| description | Abstract Pillar[n]arenes have broad applications in biological medicine, materials science, and supramolecular gels. Notably, enantiopure pillar[5]arenes are valued for their roles in enantioselective host–guest recognition, chiral sensing, asymmetric catalysis, and related fields. Current methods for obtaining chiral pillar[n]arenes rely heavily on resolution agents or chiral HPLC resolution. However, the synthesis of these compounds via asymmetric catalysis remains challenging. In this study, we develop an asymmetric extended side-arm Suzuki–Miyaura cross-coupling strategy to construct inherently chiral pillar[5]arenes with excellent yields and high enantioselectivities using a palladium catalyst and a Sadphos ligand. The reaction scope extends beyond arylboronic acids to encompass 2-arylvinylboronic acids and other multi-OTf-substituted substrates, all efficiently producing the desired products. Further exploration of the synthetic applications, along with photophysical and chiroptical analyses, confirm the potential of these chiral pillar[5]arenes for diverse applications across multiple disciplines. |
| format | Article |
| id | doaj-art-d8212b86c981409290f681b546b0bff0 |
| institution | DOAJ |
| issn | 2041-1723 |
| language | English |
| publishDate | 2025-03-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Nature Communications |
| spelling | doaj-art-d8212b86c981409290f681b546b0bff02025-08-20T02:56:15ZengNature PortfolioNature Communications2041-17232025-03-0116111210.1038/s41467-025-57461-xEnantioselective construction of inherently chiral pillar[5]arenes via palladium-catalysed Suzuki–Miyaura cross-couplingTing-Rui Luan0Che Sun1Yong-Le Tian2Yu-Kun Jiang3Long-Long Xi4Ren-Rong Liu5College of Chemistry and Chemical Engineering, Qingdao UniversityCollege of Chemistry and Chemical Engineering, Qingdao UniversityCollege of Chemistry and Chemical Engineering, Qingdao UniversityCollege of Chemistry and Chemical Engineering, Qingdao UniversityCollege of Chemistry and Chemical Engineering, Qingdao UniversityCollege of Chemistry and Chemical Engineering, Qingdao UniversityAbstract Pillar[n]arenes have broad applications in biological medicine, materials science, and supramolecular gels. Notably, enantiopure pillar[5]arenes are valued for their roles in enantioselective host–guest recognition, chiral sensing, asymmetric catalysis, and related fields. Current methods for obtaining chiral pillar[n]arenes rely heavily on resolution agents or chiral HPLC resolution. However, the synthesis of these compounds via asymmetric catalysis remains challenging. In this study, we develop an asymmetric extended side-arm Suzuki–Miyaura cross-coupling strategy to construct inherently chiral pillar[5]arenes with excellent yields and high enantioselectivities using a palladium catalyst and a Sadphos ligand. The reaction scope extends beyond arylboronic acids to encompass 2-arylvinylboronic acids and other multi-OTf-substituted substrates, all efficiently producing the desired products. Further exploration of the synthetic applications, along with photophysical and chiroptical analyses, confirm the potential of these chiral pillar[5]arenes for diverse applications across multiple disciplines.https://doi.org/10.1038/s41467-025-57461-x |
| spellingShingle | Ting-Rui Luan Che Sun Yong-Le Tian Yu-Kun Jiang Long-Long Xi Ren-Rong Liu Enantioselective construction of inherently chiral pillar[5]arenes via palladium-catalysed Suzuki–Miyaura cross-coupling Nature Communications |
| title | Enantioselective construction of inherently chiral pillar[5]arenes via palladium-catalysed Suzuki–Miyaura cross-coupling |
| title_full | Enantioselective construction of inherently chiral pillar[5]arenes via palladium-catalysed Suzuki–Miyaura cross-coupling |
| title_fullStr | Enantioselective construction of inherently chiral pillar[5]arenes via palladium-catalysed Suzuki–Miyaura cross-coupling |
| title_full_unstemmed | Enantioselective construction of inherently chiral pillar[5]arenes via palladium-catalysed Suzuki–Miyaura cross-coupling |
| title_short | Enantioselective construction of inherently chiral pillar[5]arenes via palladium-catalysed Suzuki–Miyaura cross-coupling |
| title_sort | enantioselective construction of inherently chiral pillar 5 arenes via palladium catalysed suzuki miyaura cross coupling |
| url | https://doi.org/10.1038/s41467-025-57461-x |
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