Molecular Catalysis, Journal Year: 2024, Volume and Issue: 570, P. 114685 - 114685
Published: Nov. 21, 2024
Language: Английский
ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(6), P. 4318 - 4328
Published: March 6, 2024
Sulfonyl fluorides have found increasing applications as functional molecules in chemistry and biology. We herein report a copper-catalyzed atom-economical access to two categories of sulfonyl through radical relay strategy the presence an SO2 surrogate. The aliphatic C(sp3)–H bond N-fluoro-N-alkyl sulfonamides reacted via 1,5-hydrogen atom transfer (HAT) process, affording alkanesulfonyl with proximal amino group. On other hand, utilizing substrates containing proper C═C double resulted intramolecular olefin aminofluorosulfonylation, allowing synthesis fluorosulfonyl-functionalized pyrrolidines piperidines atom-transfer addition (ATRA). Both reaction systems proceeded under mild conditions, requiring no additional fluorine source. Experimental computational studies suggest that S–F coupling is likely achieved radical-rebound pathway. By taking advantage SuFEx multifunctionality products, method applicable late-stage modification bioactive compounds, drug ligation chemistry, organic synthesis.
Language: Английский
Citations
11
Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(4), P. 1232 - 1250
Published: Dec. 28, 2023
Recent advances in HAT-induced C(sp 3 )–H functionalizations triggered by radical addition to alkynes, including 5- exo-trig , endo-trig 4- and 6- cyclization cascades, intermolecular functionalizations, are summarized.
Language: Английский
Citations
15
Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(17)
Published: Feb. 21, 2024
As a type of elementary organic compounds containing N-N single bond, hydrazone involved chemical conversions are extremely extensive, but they mainly limited to N
Language: Английский
Citations
4
ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(10), P. 8005 - 8012
Published: May 9, 2024
We report intra- and intermolecular γ-amino C(sp3)–H functionalization of aliphatic amines using a vinylsulfone-based HAT (hydrogen atom transfer) auxiliary triple catalysis, which is composed photoredox, cobalt, Brønsted acid catalysts under visible light irradiation. The process accomplishes four elementary steps: (i) electrophilic carbon-centered radical formation on the via MHAT (metal hydride hydrogen reaction, (ii) generation through 1,6-HAT (iii) single-electron oxidation to carbocation equivalents, (iv) nucleophilic substitution with internal or external nucleophiles. As result, this afforded γ-amino-functionalized products, such as azetidines, 1,3-diamine, 1,3-aminoalcohol derivatives.
Language: Английский
Citations
4
Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(45)
Published: July 8, 2024
Inherently chiral calix[4]arenes represent a unique type of molecules with significant applications, yet their catalytic enantioselective synthesis remains largely underexplored. We report herein the inherently through sequential organocatalyzed Povarov reaction and aromatizations. The phosphoric acid catalyzed three-component involving amino group-substituted calix[4]arenes, aldehydes (di)enamides desymmetrized prochiral calix[4]arene substrates, which was followed by various aromatization methods, resulting in diverse array novel quinoline-containing good yields high enantioselectivities (up to 75 % yield, 99 ee). large-scale derivatizations products highlight value this method. Furthermore, preliminary exploration into photophysical chiroptical properties demonstrate potential applications these molecules.
Language: Английский
Citations
4
Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134451 - 134451
Published: Jan. 1, 2025
Language: Английский
Citations
0
The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown
Published: Feb. 10, 2025
A trifluoromethylpyridylation of unactivated alkenes in aqueous solution under open air is reported. This process allows the incorporation trifluoromethyl and construction pyridines annulated to saturated cycles via an intramolecular Minisci reaction using Langlois' reagent (CF3SO2Na) as a source. Extrusion from not required. broad functional group tolerance observed. series five-, six-, seven-membered are obtained, exhibiting great potential application preparation diversified pyridines.
Language: Английский
Citations
0
Asian Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown
Published: March 10, 2025
Abstract A visible‐light‐promoted C−H amidation of (hetero)arenes with hypervalent iodine reagents has been successfully achieved good yields. The high efficiency, broad substrate range and functional group compatibility demonstrated the utility method. Moreover, this protocol was suitable for late‐stage functionalization natural products. Mechanistic studies have shown that N‐centred saccharin radical mediates arenes.
Language: Английский
Citations
0
Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134666 - 134666
Published: April 1, 2025
Language: Английский
Citations
0
European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(13)
Published: Feb. 15, 2024
Abstract Direct C−H functionalization is an important strategy for the rapid synthesis of valuable organic molecules. Radical‐involved remote C(sp 3 )‐H based on hydrogen atom transfer (HAT) becomes method enabling selective direct transformation bonds at specific distal position(s). In recent years, copper‐catalyzed fluoroamide‐directed bond through intramolecular HAT has served as a robust and elegant assembly variety functionalized (sulfon)amides related derivatives. This review focuses advances in this area. These transformations proceed effectively with high selectivities good functional group compatibility under mild conditions.
Language: Английский
Citations
3