Catalytic asymmetric C–N cross-coupling towards boron-stereogenic 3-amino-BODIPYs
Abstract 3-Amino boron dipyrromethenes (BODIPYs) are a versatile class of fluorophores widely utilized in live cell imaging, photodynamic therapy, and fluorescent materials science. Despite the growing demand for optically active BODIPYs, the synthesis of chiral 3-amino-BODIPYs, particularly the cat...
Saved in:
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Nature Portfolio
2025-01-01
|
| Series: | Nature Communications |
| Online Access: | https://doi.org/10.1038/s41467-024-55796-5 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1841544515141238784 |
|---|---|
| author | Baoquan Zhan Li-Qing Ren Jiayi Zhao Hua Zhang Chuan He |
| author_facet | Baoquan Zhan Li-Qing Ren Jiayi Zhao Hua Zhang Chuan He |
| author_sort | Baoquan Zhan |
| collection | DOAJ |
| description | Abstract 3-Amino boron dipyrromethenes (BODIPYs) are a versatile class of fluorophores widely utilized in live cell imaging, photodynamic therapy, and fluorescent materials science. Despite the growing demand for optically active BODIPYs, the synthesis of chiral 3-amino-BODIPYs, particularly the catalytic asymmetric version, remains a challenge. Herein, we report the synthesis of boron-stereogenic 3-amino-BODIPYs via a palladium-catalyzed desymmetric C–N cross-coupling of prochiral 3,5-dihalogen-BODIPYs. This approach features a broad substrate scope, excellent functional group tolerance, high efficiency, and remarkable enantioselectivities, under mild reaction conditions. Further stereospecific formation of chiral 3,5-diamino-BODIPYs, along with an investigation into the photophysical properties of the resulting optical BODIPYs are also explored. This asymmetric protocol not only enriches the chemical space of chiroptical BODIPY dyes but also contributes to the realm of chiral boron chemistry. |
| format | Article |
| id | doaj-art-6c86b04dbe304cb4ac5953216c30d0b8 |
| institution | Kabale University |
| issn | 2041-1723 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Nature Communications |
| spelling | doaj-art-6c86b04dbe304cb4ac5953216c30d0b82025-01-12T12:30:01ZengNature PortfolioNature Communications2041-17232025-01-011611810.1038/s41467-024-55796-5Catalytic asymmetric C–N cross-coupling towards boron-stereogenic 3-amino-BODIPYsBaoquan Zhan0Li-Qing Ren1Jiayi Zhao2Hua Zhang3Chuan He4Key Laboratory of Catalysis and Energy Materials Chemistry of Ministry of Education, Hubei Key Laboratory of Catalysis and Materials Science, School of Chemistry and Materials Science, South-Central Minzu UniversityShenzhen Grubbs Institute and Department of Chemistry, Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and TechnologyShenzhen Grubbs Institute and Department of Chemistry, Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and TechnologyKey Laboratory of Catalysis and Energy Materials Chemistry of Ministry of Education, Hubei Key Laboratory of Catalysis and Materials Science, School of Chemistry and Materials Science, South-Central Minzu UniversityShenzhen Grubbs Institute and Department of Chemistry, Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and TechnologyAbstract 3-Amino boron dipyrromethenes (BODIPYs) are a versatile class of fluorophores widely utilized in live cell imaging, photodynamic therapy, and fluorescent materials science. Despite the growing demand for optically active BODIPYs, the synthesis of chiral 3-amino-BODIPYs, particularly the catalytic asymmetric version, remains a challenge. Herein, we report the synthesis of boron-stereogenic 3-amino-BODIPYs via a palladium-catalyzed desymmetric C–N cross-coupling of prochiral 3,5-dihalogen-BODIPYs. This approach features a broad substrate scope, excellent functional group tolerance, high efficiency, and remarkable enantioselectivities, under mild reaction conditions. Further stereospecific formation of chiral 3,5-diamino-BODIPYs, along with an investigation into the photophysical properties of the resulting optical BODIPYs are also explored. This asymmetric protocol not only enriches the chemical space of chiroptical BODIPY dyes but also contributes to the realm of chiral boron chemistry.https://doi.org/10.1038/s41467-024-55796-5 |
| spellingShingle | Baoquan Zhan Li-Qing Ren Jiayi Zhao Hua Zhang Chuan He Catalytic asymmetric C–N cross-coupling towards boron-stereogenic 3-amino-BODIPYs Nature Communications |
| title | Catalytic asymmetric C–N cross-coupling towards boron-stereogenic 3-amino-BODIPYs |
| title_full | Catalytic asymmetric C–N cross-coupling towards boron-stereogenic 3-amino-BODIPYs |
| title_fullStr | Catalytic asymmetric C–N cross-coupling towards boron-stereogenic 3-amino-BODIPYs |
| title_full_unstemmed | Catalytic asymmetric C–N cross-coupling towards boron-stereogenic 3-amino-BODIPYs |
| title_short | Catalytic asymmetric C–N cross-coupling towards boron-stereogenic 3-amino-BODIPYs |
| title_sort | catalytic asymmetric c n cross coupling towards boron stereogenic 3 amino bodipys |
| url | https://doi.org/10.1038/s41467-024-55796-5 |
| work_keys_str_mv | AT baoquanzhan catalyticasymmetriccncrosscouplingtowardsboronstereogenic3aminobodipys AT liqingren catalyticasymmetriccncrosscouplingtowardsboronstereogenic3aminobodipys AT jiayizhao catalyticasymmetriccncrosscouplingtowardsboronstereogenic3aminobodipys AT huazhang catalyticasymmetriccncrosscouplingtowardsboronstereogenic3aminobodipys AT chuanhe catalyticasymmetriccncrosscouplingtowardsboronstereogenic3aminobodipys |