Fe-Catalyzed Radical Trifluoromethylation and Cyclization of Ortho-Vinyl Enaminones with 1-(Trifluoromethyl)-1,3-benzo-[d][1,2]iodaoxol-3(1H)-one to Construct Functionalized Quinolines DOI

Qin Luo,

Z.‐F. XIE,

Cen Jian

и другие.

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

Опубликована: Май 19, 2025

Herein, we present a protocol for the construction of functionalized quinolines, i.e., 3-acyl-4-(2,2,2-trifluoro-ethyl)quinolines (ATFQLs) 4, from ortho-vinyl enaminones and 1-(trifluoromethyl)-1,3-benzo-[d][1,2]-iodaoxol-3(1H)-one, which was catalyzed by FeCp2 promoted FeCl3 (Lewis acid) additives in solvents (i.e., acetonitrile toluene). This strategy first utilized FeCp2-catalyzed functionalization alkenes with trifluoromethyl radicals. The intermediate formed captured ortho-iodobenzoate substrate, yielding 3, then underwent FeCl3-catalyzed elimination at higher temperature to form an α,β-unsaturated intermediate. subsequent intramolecular Michael reaction yielded final target compound 4. In summary, series ATFQLs 4 were synthesized through formation two bonds (C═C C-C).

Язык: Английский

Photoredox-Mediated Radical Addition/Cyclization To Construct Benzannulated 6,5-Spiroketal Glycosides DOI
Chen Li, Shouyun Yu

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Янв. 30, 2025

We herein present a green and mild photoredox strategy for constructing framework of benzannulated 6,5-spiroketal glycosides. This method employs various O-arylacetylene glycosides aryl ketone acids as the starting materials, facilitating rapid straightforward synthesis with up to 92% yields under catalytic conditions. efficient approach has potential significantly enhance molecular library carbohydrate-based pharmaceuticals.

Язык: Английский

Процитировано

0
Visible‐Light‐Induced C−H Amidation of (Hetero)arenes with Hypervalent Iodine(III) Reagents DOI Open Access
Xiaojuan Wang, He Wang, Zhenkun Ma

и другие.

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

Опубликована: Март 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.

Язык: Английский

Процитировано

0
Fe-Catalyzed Radical Trifluoromethylation and Cyclization of Ortho-Vinyl Enaminones with 1-(Trifluoromethyl)-1,3-benzo-[d][1,2]iodaoxol-3(1H)-one to Construct Functionalized Quinolines DOI

Qin Luo,

Z.‐F. XIE,

Cen Jian

и другие.

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

Опубликована: Май 19, 2025

Herein, we present a protocol for the construction of functionalized quinolines, i.e., 3-acyl-4-(2,2,2-trifluoro-ethyl)quinolines (ATFQLs) 4, from ortho-vinyl enaminones and 1-(trifluoromethyl)-1,3-benzo-[d][1,2]-iodaoxol-3(1H)-one, which was catalyzed by FeCp2 promoted FeCl3 (Lewis acid) additives in solvents (i.e., acetonitrile toluene). This strategy first utilized FeCp2-catalyzed functionalization alkenes with trifluoromethyl radicals. The intermediate formed captured ortho-iodobenzoate substrate, yielding 3, then underwent FeCl3-catalyzed elimination at higher temperature to form an α,β-unsaturated intermediate. subsequent intramolecular Michael reaction yielded final target compound 4. In summary, series ATFQLs 4 were synthesized through formation two bonds (C═C C-C).

Язык: Английский

Процитировано

0