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.
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http://dx.doi.org/10.1038/s41467-024-55796-5 | DOI Listing |
Nat Commun
January 2025
Shenzhen 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 Technology, Shenzhen, Guangdong, China.
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.
View Article and Find Full Text PDFJ Am Chem Soc
January 2025
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, United States.
Reported herein is the synthesis of a novel chiral dicarboxylic ligand for Mn(II) and the application of the Mn complex to the highly enantio- and position-selective epoxidation of C═C under mild conditions, even with polyolefinic substrates. A stereomechanistic basis for asymmetric induction is suggested.
View Article and Find Full Text PDFInt J Biol Macromol
January 2025
Key Laboratory of Organosilicon Chemistry and Materials Technology, Ministry of Education; College of Materials Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, Zhejiang 311121, China. Electronic address:
Keto reductases are crucial NAD(P)H-dependent enzymes used for the enantioselective synthesis of alcohols from prochiral ketones. Typically, the NADPH cofactor is regenerated through a second enzyme and/or substrate. However, photocatalytic cofactor regeneration using water as a sacrificial electron and hydrogen donor presents a promising alternative, albeit a challenging one.
View Article and Find Full Text PDFOrg Lett
January 2025
Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism, Shanghai Key Laboratory of New Drug Design, and School of Pharmacy, East China University of Science and Technology, Shanghai 200237, P. R. China.
The efficient construction of chiral aryl-containing organosilicon frameworks via catalytic enantioselective three-component silylarylation of alkenes remains a great challenge. Herein, a photoredox/nickel dual-catalytic asymmetric protocol has been disclosed by using a chiral biimidazoline (BiIM) as the ligand, silylboranes as the silyl radical precursors, aryl bromides as the coupling partners, and morpholine as the promoter. Remarkably, the reaction features mild and green conditions, high reaction efficiency, and excellent enantioselectivity, enabling the facile synthesis of valuable chiral tropic acid and sila-isoflavanone structures.
View Article and Find Full Text PDFACS Macro Lett
January 2025
Institute for Molecules and Materials, Radboud University, Heyendaalseweg 135 6525 AJ, Nijmegen, The Netherlands.
Lactide, possessing two stereocenters and thus three distinct configurations (DD, DL, and LL), serves as a captivating building block for polymers and self-assembly. Notably, polylactide (PLA) exhibits stereocomplexation, displaying heightened interactions between different configurations compared with interactions within the same configuration. This characteristic renders PLA an intriguing subject for investigating self-assembly behavior.
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