Visible-light-promoted Radical Cyclization/Arylation Cascade for the Construction of α,α-Difluoro-γ-Lactam-Fused Quinoxalin-2(1H)-Ones

被引：27

作者：

Zhang, Yun-Chao ^{[1
]}

Chen, Yang ^{[1
]}

Sun, Jing ^{[1
]}

Wang, Jing-Yun ^{[1
]}

Zhou, Ming-Dong ^{[1
]}

机构：

[1] Liaoning Petrochem Univ, Sch Petrochem Engn, Fushun 113001, Liaoning, Peoples R China

来源：

CHINESE JOURNAL OF CHEMISTRY | 2022年 / 40卷 / 06期

基金：

中国国家自然科学基金;

关键词：

Photocatalysis; Cyclization; Radicals; Fluoro-gamma-lactams; Quinoxalin-2(1H)-ones; EXTERNAL PHOTOSENSITIZER-FREE; C-H FUNCTIONALIZATION; ARYL ACYL PEROXIDES; DECARBOXYLATIVE C3-DIFLUOROARYLMETHYLATION; GEM-DIFLUOROALKENES; METAL CATALYST; ALKYLATION; ARYLATION; QUINOXALIN-2(H)-ONES; TRIFLUOROMETHYLATION;

D O I：

10.1002/cjoc.202100787

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A visible-light-induced tandem radical intramolecular cyclization/arylation of quinoxalin-2(1H)-ones with bromodifluoroacetamides is described. This protocol allows efficient access to a variety of valuable alpha,alpha-difluoro-gamma -lactam-fused quinoxalin-2(1H)-ones in moderate to good yields under metal-free, mild and redox neutral reaction conditions. This strategy is tolerant of various functional groups and a broad range of substrates. The mechanism experiments suggested an involvement of 5-exo-trig cyclization and a radical process in this transformation. [GRAPHICS] .

引用

页码：713 / 718

页数：6

共 71 条

[1] Synthesis of certain substituted quinoxalines as antimicrobial agents (part II) [J].

Badran, MM ;

Abouzid, KAM ;

Hussein, MHM .

ARCHIVES OF PHARMACAL RESEARCH, 2003, 26 (02) :107-113

[2] Visible-light-promoted acridine red catalyzed aerobic oxidative decarboxylative acylation of α-oxo-carboxylic acids with quinoxalin-2(1H)-ones [J].

Bao, Pengli ;

Liu, Fei ;

Lv, Yufen ;

Yue, Huilan ;

Li, Jiang-Sheng ;

Wei, Wei .

ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (03) :492-498

[3] Mechanistic Studies in Photocatalysis [J].

Buzzetti, Luca ;

Crisenza, Giacomo E. M. ;

Melchiorre, Paolo .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (12) :3730-3747

[4] Application of Photosensitizer 2,4,5,6-Tetrakis(carbazol-9-yl)-1,3-dicyanobenzene in Photo-induced Transition-Metal-Free Organic Synthesis [J].

Chen, Jinyang ;

Li, Yuhan ;

Mei, Lan ;

Wu, Hongyu .

CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (11) :3040-3050

[5] C4-arylation and domino C4-arylation/3,2-carbonyl migration of indoles by tuning Pd catalytic modes: Pd(i)-Pd(ii) catalysis vs. Pd(ii) catalysis [J].

Cheng, Yaohang ;

Yu, Shijie ;

He, Yuhang ;

An, Guanghui ;

Li, Guangming ;

Yang, Zhenyu .

CHEMICAL SCIENCE, 2021, 12 (09) :3216-3225

[6] Ruthenium(II)-catalyzed para-selective C??H difluoroalkylation of aromatic aldehydes and ketones using transient directing groups [J].

Cheng, Yaohang ;

He, Yuhang ;

Zheng, Jie ;

Yang, Hui ;

Liu, Jun ;

An, Guanghui ;

Li, Guangming .

CHINESE CHEMICAL LETTERS, 2021, 32 (04) :1437-1441

[7] Metal-Free Direct C-H Functionalization of Quinoxalin-2(1H)-Ones to Produce 3-Vinylated Quinoxalin-2(1H)-Ones in the Presence of Alkenes [J].

Ding, Rongcai ;

Li, Yingxue ;

Chang, Yaoyao ;

Liu, Yue ;

Yu, Jie ;

Lv, Yanna ;

Hu, Jinxing .

FRONTIERS IN CHEMISTRY, 2021, 9

[8] Electrochemical Minisci-type trifluoromethylation of electron-deficient heterocycles mediated by bromide ions [J].

Dou, Gui-Yuan ;

Jiang, Yang-Ye ;

Xu, Kun ;

Zeng, Cheng-Chu .

ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (14) :2392-2397

[9] Synthesis of gem-Difluoroalkenes via Zn-Mediated Decarboxylative/Defluorinative Cross-Coupling [J].

Du, Hai-Wu ;

Chen, Yang ;

Sun, Jing ;

Gao, Qi-Sheng ;

Wang, He ;

Zhou, Ming-Dong .

ORGANIC LETTERS, 2020, 22 (23) :9342-9345

[10] Synthesis of Monofluoroalkenes through Visible-Light-Promoted Defluorinative Alkylation of gem-Difluoroalkenes with 4-Alkyl-1,4-dihydropyridines [J].

Du, Hai-Wu ;

Sun, Jing ;

Gao, Qi-Sheng ;

Wang, Jing-Yun ;

Wang, He ;

Xu, Zhaoqing ;

Zhou, Ming-Dong .

ORGANIC LETTERS, 2020, 22 (04) :1542-1546

← 1 2 3 4 5 6 7 8 →