Molecules, Journal Year: 2025, Volume and Issue: 30(11), P. 2305 - 2305
Published: May 24, 2025
This perspective highlights current trends and recent advances in the introduction of fluorine fluoroalkyl moieties into furanic core biobased furfural-derived furans. Existing potential applications these fluorinated building blocks development pharmaceuticals advanced materials are also discussed.
Language: Английский
Organic Letters, Journal Year: 2025, Volume and Issue: unknown
Published: Feb. 3, 2025
A Ru-catalyzed defluorinative cyclization of polyfluoroalkyl tetralones has been developed under visible-light irradiation for the precise assembly γ-pyrones featuring α-perfluoroalkyl and β-fluorine substituents. Selective functionalization five C(sp3)–F bonds at three carbon sites on perfluoroalkyl chain provides a new mode utilizing polyfluorides as versatile synthons to access difficult-to-obtain heterocyclic scaffolds. Moreover, sulfinate salt serves dual roles an oxygen source creating carbonyl group defluorinating promoter.
Language: Английский
Citations
3
The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown
Published: Feb. 23, 2025
Trifluoromethyl enone emerges as a versatile and multifaceted building block in organic synthesis. A defluorinative heterocyclization reaction of readily available β,β-ditrifluoromethylated enones biocompatible sodium sulfinates has been developed for the modular synthesis densely functionalized furans with regio-defined C2,4-bissulfonyl C3-trifluoromethyl substitutions. This three-component method proceeds through sequential sulfonylation intramolecular O-cyclization, enabling assembly one furan ring, formation C-SO2/C–O bonds, cleavage three C(sp3)-F bonds one-pot manner under transition metal-free conditions. Moreover, obtained product can further react benzyne precursor to generate 1,4-epoxynaphthalene Diels–Alder cycloaddition. The is also distinguished by its broad substrate scope, excellent functional group tolerance, scalability.
Language: Английский
Citations
1
Organic Letters, Journal Year: 2025, Volume and Issue: unknown
Published: Feb. 26, 2025
A chemo-, regio-, and stereoselective condensation reaction of perfluoroalkyl alkynes (PFAAs), (CH2O)n, (NH4)2CO3 through the cleavage five inert C(sp3)-F bonds at three distinct carbon sites, thereby establishing an unprecedented platform for synthesizing structurally unique (E)-(2-amino-fluoroalkenyl)pyrimidines, is first developed. Remarkably, this features mild conditions, good compatibility with various functional groups, excellent E-stereoselectivity, late-stage modification complex molecules, scalability, versatile synthetic transformations resulting heterocyclic compounds.
Language: Английский
Citations
1
Organic Letters, Journal Year: 2025, Volume and Issue: unknown
Published: March 28, 2025
Pyridines represent privileged heterocycles, and the ability to produce fluorinated pyridines from polyfluorinated substances through selective defluorofunctionalization is a new addition their synthesis. Herein, an unprecedented formal [4+2] defluorocycloaddition of perfluoroalkyl alkynes benzylamines under metal-free conditions described. By leveraging functionalization four C(sp3)–F bonds on two vicinal sterically hindered carbons alkynes, diverse array meta-fluoroalkylated pyridin-4-amines were synthesized with good functional group tolerance. The mechanistic studies revealed sequence hydroamination, successive defluorination, 6π-electrocyclization, aromatization, amination.
Language: Английский
Citations
1
The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown
Published: April 9, 2025
Perfluoroalkyl alkenyl iodides (PFAIs) are emerging as highly reactive, storage-stable, and multifunctional fluoroalkyl-bearing reagents, facilitating the manufacture of value-added organofluorides through multi-halo-functionalization. Herein, we developed a water-involved 1,3-aminoxylation PFAIs with sulfonamides for chemo-, regio-, Z-stereoselective synthesis valuable β-fluoroacyl vinylamines. This reaction proceeded via sequential deiodoamination defluoroxylation process under transition-metal-free conditions, featuring broad substrate scope good functional group tolerance. Compared to reported methods, some drawbacks, such multistep manipulation, harsh need expensive catalysts, use toxic/sensitive could be eliminated. Furthermore, synthetic potential this method was demonstrated scale-up synthesis, postfunctionalization complex molecules, ready transformation products.
Language: Английский
Citations
0
Molecules, Journal Year: 2025, Volume and Issue: 30(8), P. 1832 - 1832
Published: April 19, 2025
A novel method for the efficient and straightforward synthesis of tetrasubstituted furans is presented, employing a base-catalyzed reaction α-hydroxy ketones cyano compounds. The proceeds under relatively mild conditions, utilizes readily available starting materials, exhibits good functional group tolerance high yields. Notably, this obviates need expensive metal catalysts introduces crucial groups such as amino moieties. Furthermore, it avoids prerequisite functionalization substrates, thereby enhancing atomic economy.
Language: Английский
Citations
0
Molecules, Journal Year: 2025, Volume and Issue: 30(11), P. 2305 - 2305
Published: May 24, 2025
This perspective highlights current trends and recent advances in the introduction of fluorine fluoroalkyl moieties into furanic core biobased furfural-derived furans. Existing potential applications these fluorinated building blocks development pharmaceuticals advanced materials are also discussed.
Language: Английский
Citations
0