Synthesis of trans‐2‐(Disubstituted‐amino)alkenyl Polyoxyperfluoroalkyl Ketones from Tertiary Amines and Perfluoroalkyl Ether Carboxylates Featuring “–CF2O–” Units DOI
Qijian Ni, Shiyu Zhao, Cheng‐Ying Wu

и другие.

Chinese Journal of Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 25, 2025

Comprehensive Summary A one‐pot transformation of aliphatic and aromatic tertiary amines to novel fluorinated enaminones has been developed, utilizing perfluoroalkyl ether carboxylates (PFECA salts) featuring “–CF 2 O–” units as the fluorine‐containing reagents. Carbonyl fluoride, acyl fluorides anhydrides by thermal decomposition these PFECA salts were proposed act key active species that trigger tandem oxidation–acylation process amines, through enamine intermediates.

Язык: Английский

Sulfinate-Promoted Defluorinative Cyclization of Polyfluoroalkyl Tetralones Enabled by Photocatalysis DOI

Ming-Yao Tang,

M Kellis, Xiaoxiao Sun

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 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.

Язык: Английский

Процитировано

3

[4+2] Defluorocycloaddition of Perfluoroalkyl Alkynes and Benzylamines: Synthesis of meta-Fluoroalkylated Pyridin-4-amines DOI
Xueying Huang, Jiawei Chen,

D.‐L. CHEN

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 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.

Язык: Английский

Процитировано

0

Water-Involved 1,3-Aminoxylation of Fluoroalkenes: Chemo-, Regio-, and Stereoselective Synthesis of β-Fluoroacyl Vinylamines DOI
Chi Zhang, Xueying Huang,

Shu-Ji Gao

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 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.

Язык: Английский

Процитировано

0

Synthesis of trans‐2‐(Disubstituted‐amino)alkenyl Polyoxyperfluoroalkyl Ketones from Tertiary Amines and Perfluoroalkyl Ether Carboxylates Featuring “–CF2O–” Units DOI
Qijian Ni, Shiyu Zhao, Cheng‐Ying Wu

и другие.

Chinese Journal of Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 25, 2025

Comprehensive Summary A one‐pot transformation of aliphatic and aromatic tertiary amines to novel fluorinated enaminones has been developed, utilizing perfluoroalkyl ether carboxylates (PFECA salts) featuring “–CF 2 O–” units as the fluorine‐containing reagents. Carbonyl fluoride, acyl fluorides anhydrides by thermal decomposition these PFECA salts were proposed act key active species that trigger tandem oxidation–acylation process amines, through enamine intermediates.

Язык: Английский

Процитировано

0