Chemical Science, Год журнала: 2025, Номер unknown
Опубликована: Янв. 1, 2025
Catalytic insertion of nitrenes into B–H bonds produces unique compounds with chiral boron atoms.
Язык: Английский
Nature Chemistry, Год журнала: 2024, Номер 16(1), С. 42 - 53
Опубликована: Янв. 1, 2024
Язык: Английский
Процитировано
27
Nature Communications, Год журнала: 2025, Номер 16(1)
Опубликована: Янв. 7, 2025
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, synthesis chiral 3-amino-BODIPYs, particularly catalytic asymmetric version, remains challenge. Herein, we report boron-stereogenic 3-amino-BODIPYs via palladium-catalyzed desymmetric C–N cross-coupling prochiral 3,5-dihalogen-BODIPYs. This approach features broad substrate scope, excellent functional group tolerance, high efficiency, remarkable enantioselectivities, under mild reaction conditions. Further stereospecific formation 3,5-diamino-BODIPYs, along with an investigation into photophysical properties resulting optical BODIPYs also explored. protocol not only enriches chemical space chiroptical BODIPY dyes but contributes to realm chemistry. (BODIPYs), which useful science, authors first cross-couplings.
Язык: Английский
Процитировано
3
Coordination Chemistry Reviews, Год журнала: 2021, Номер 453, С. 214329 - 214329
Опубликована: Дек. 13, 2021
Язык: Английский
Процитировано
67
Journal of the American Chemical Society, Год журнала: 2022, Номер 144(15), С. 6981 - 6991
Опубликована: Апрель 8, 2022
Significant advances have been achieved for the construction of chiral skeletons containing 1,2,3-triazoles via transition-metal-catalyzed asymmetric azide–alkyne cycloaddition; however, most them limited to terminal alkynes in synthesis central chirality desymmetrization and dynamic/dynamic kinetic resolution. Enantioselective azide-internal-alkyne cycloaddition is extremely limited. Moreover, a challenging five-membered (hetero)biaryl axially molecule still underexplored. Herein, we first report an atroposelective atom-economical 1,4,5-trisubstituted 1,2,3-triazoles, directly acting as core units atropisomers, enantioselective Rh-catalyzed (E-RhAAC) internal azides. The reaction demonstrates excellent functional group tolerance, forging variety C–C under mild conditions with moderate yields (up 99% yield) generally high enantioselectivities ee) along specific regiocontrol. origin regio- enantioselectivity control disclosed by density theory (DFT) calculations, providing new guidance facile compounds.
Язык: Английский
Процитировано
57
Journal of the American Chemical Society, Год журнала: 2022, Номер 144(46), С. 21347 - 21355
Опубликована: Ноя. 11, 2022
The first copper-catalyzed enantioselective [4 + 1] annulation of yne-allylic esters with 1,3-dicarbonyl compounds was realized through an elegant remote stereocontrol strategy. very ε regioselective nucleophilic substitution developed by employing a novel chiral copper-vinylvinylidene species from the new C4 synthon esters. Thus, greatly diverse spirocycles were obtained ample scope and excellent levels chemo-, regio-, enantioselectivities. Moreover, detailed mechanistic studies suggest Conia-ene cascade pathway on stereochemical induction progress.
Язык: Английский
Процитировано
43
Nature Synthesis, Год журнала: 2023, Номер 2(11), С. 1020 - 1036
Опубликована: Окт. 16, 2023
Язык: Английский
Процитировано
39
Chemical Communications, Год журнала: 2023, Номер 59(26), С. 3812 - 3820
Опубликована: Янв. 1, 2023
Tetracoordinate boron compounds are a highly important class of molecules, which the key intermediates in many organoboron-related chemical transformations and have unique luminescence properties.
Язык: Английский
Процитировано
29
Nature Synthesis, Год журнала: 2023, Номер 2(6), С. 564 - 571
Опубликована: Март 16, 2023
Язык: Английский
Процитировано
25
Chemical Society Reviews, Год журнала: 2023, Номер 52(13), С. 4381 - 4391
Опубликована: Янв. 1, 2023
Four-coordinate organoboron derivatives present interesting chemical, physical, biological, electronical, and optical properties. Given the increasing demand for synthesis of smart functional materials based on chiral compounds, exploration stereoselective boron-stereogenic organo-derivatives is highly desirable. However, construction compounds stereogenic at boron has been far less studied than other elements main group due to configurational stability concerns. Nowadays, these species are no longer elusive configurationally stable have highlighted. The idea show potential building four-coordinate centre encourage future endeavors developments in field.
Язык: Английский
Процитировано
24
Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(18)
Опубликована: Март 7, 2023
We report the first highly selective kinetic resolution of racemic α-chiral azides via Cu-catalyzed azide-alkyne cycloaddition (CuAAC). Newly developed pyridine-bisoxazoline (PYBOX) ligands, bearing a C4 sulfonyl group, enable effective derived from privileged scaffolds such as indanone, cyclopentenone, and oxindole, their asymmetric CuAAC to afford α-tertiary 1,2,3-triazoles with high excellent ee values. DFT calculations control experiments reveal that group decreases Lewis basicity ligand increases electrophilicity copper center for better recognition azides, functions shielding make chiral pocket catalyst more effective.
Язык: Английский
Процитировано
23