Cascade Reactions of α-Carbonyl Radicals Enabled by Photocatalytic Hydrogen Atom Transfer for the Synthesis of Benzonaphthyridinone Derivatives DOI

Zhike Zhou,

Xian‐Li Ma, Zhanqiang Jian

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Май 27, 2025

A metal-free photocatalytic addition/cyclization of the α-carbonyl radical with N-(2-cyanophenyl)acrylamides has been developed, providing novel benzonaphthyridinone scaffolds in moderate to good yields. Arylsulfonium salt was employed as a hydrogen atom abstractor, which effectively converts various ketones into radicals. This protocol advantages including simple and mild conditions, broad substrate scope, remarkable tolerance toward diverse functional groups.

Язык: Английский

Photocatalytic Radical Cascade Cyclization of N-(o-Cyanobiaryl)acrylamides with Sulfonyl Chlorides DOI
Min Gao, Jian-Hong Fan, Yu Liu

и другие.

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

Опубликована: Апрель 2, 2025

A photoredox-catalyzed radical cascade cyclization of N-(o-cyanobiaryl)acrylamides with sulfonyl chlorides for the construction sulfonyl-containing pyrido[4,3,2-gh]phenanthridines has been disclosed. The developed synthetic tool tolerates a broad range to undergo sequence, including addition, nitrile insertion, and cyclization.

Язык: Английский

Процитировано

1

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

Cascade Reactions of α-Carbonyl Radicals Enabled by Photocatalytic Hydrogen Atom Transfer for the Synthesis of Benzonaphthyridinone Derivatives DOI

Zhike Zhou,

Xian‐Li Ma, Zhanqiang Jian

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Май 27, 2025

A metal-free photocatalytic addition/cyclization of the α-carbonyl radical with N-(2-cyanophenyl)acrylamides has been developed, providing novel benzonaphthyridinone scaffolds in moderate to good yields. Arylsulfonium salt was employed as a hydrogen atom abstractor, which effectively converts various ketones into radicals. This protocol advantages including simple and mild conditions, broad substrate scope, remarkable tolerance toward diverse functional groups.

Язык: Английский

Процитировано

0