A5074023932- Catalytic C–H Functionalization Methods
- Sulfur-Based Synthesis Techniques
- Lung Cancer Treatments and Mutations
- Cancer therapeutics and mechanisms
- Radical Photochemical Reactions
- Synthesis and Catalytic Reactions
- Lung Cancer Research Studies
- Chemical synthesis and alkaloids
- Traditional and Medicinal Uses of Annonaceae
- Asymmetric Synthesis and Catalysis
- Quinazolinone synthesis and applications
- N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
- HER2/EGFR in Cancer Research
- Fluorine in Organic Chemistry
- Synthesis and Biological Activity
- Catalytic Cross-Coupling Reactions
Korea Advanced Institute of Science and Technology
2019-2022
Institute for Basic Science
2019-2020
Korea Research Institute of Chemical Technology
2015-2019
Korea University of Science and Technology
2015-2019
Daejeon University
2018
Abstract N‐Alkenoxypyridinium salts have been used as synthons for the umpolung reaction of enolates preparation α‐functionalized carbonyl compounds. In contrast, we found that photoreduction N‐alkenoxypyridinium generates α‐carbonyl radicals after cleavage N−O bond, thereby allowing simultaneous incorporation α‐keto and pyridyl groups across unactivated alkenes. process, formed engage alkenes to afford alkyl radical intermediates poised subsequent addition pyridinium salts, which ultimately...
Abstract A catalytic method for the enantioselective and C4-selective functionalization of pyridine derivatives is yet to be developed. Herein, we report an efficient asymmetric β-pyridylations enals that involve N-heterocyclic carbene (NHC) catalysis with excellent control over enantioselectivity pyridyl C4-selectivity. The key strategy precise stereocontrol involves enhancing interactions between chiral NHC-bound homoenolate pyridinium salt in presence hexafluorobenzene, which effectively...
A novel visible-light-enabled alkoxy radical ring-closure and pyridylation from <italic>N</italic>-alkenyloxypyridinium salts was achieved under metal-free mild conditions, offering a powerful synthetic tool for assembling various pyridine-tethered tetrahydrofurans.
Although N-alkenoxyheteroarenium salts have been widely used as umpoled synthons with nucleophilic (hetero)arenes, the use of electron-poor heteroarenes has remained unexplored. To overcome inherent electron deficiency quinolinium salts, a traceless nucleophile-triggered strategy was designed, wherein segment is converted into dearomatized intermediate, thereby allowing simultaneous C8-functionalization quinolines at room temperature. Experimental and computational studies support operation...
Abstract N‐Alkenoxypyridinium salts have been used as synthons for the umpolung reaction of enolates preparation α‐functionalized carbonyl compounds. In contrast, we found that photoreduction N‐alkenoxypyridinium generates α‐carbonyl radicals after cleavage N−O bond, thereby allowing simultaneous incorporation α‐keto and pyridyl groups across unactivated alkenes. process, formed engage alkenes to afford alkyl radical intermediates poised subsequent addition pyridinium salts, which ultimately...
A novel approach for the addition of tertiary trifluoromethylcarbinols at β-position cyclic enamides has been developed.
A mild one‐pot and metal‐free condition was discovered to implement two different alkyl groups chemoselectively on 1‐methyl‐3,4‐dihydroisoquinoline (1‐Me‐DHIQ), one at the nitrogen another C1‐methyl group. This chemistry is compatible with various DHIQs as well halides. Application of this facilitated concise syntheses methopholine, (±)‐homolaudanosine, (±)‐dysoxyline, requiring only steps from 6,7‐dimethoxy‐1‐Me‐DHIQ.
Abstract Although N‐alkenoxyheteroarenium salts have been widely used as umpoled synthons with nucleophilic (hetero)arenes, the use of electron‐poor heteroarenes has remained unexplored. To overcome inherent electron deficiency quinolinium salts, a traceless nucleophile‐triggered strategy was designed, wherein segment is converted into dearomatized intermediate, thereby allowing simultaneous C8‐functionalization quinolines at room temperature. Experimental and computational studies support...