Photoinduced tandem radical cyclization/heteroarylation of N-allylbromodifluoroacetamides with quinoxalin-2(1H)-ones or coumarins under metal- and photocatalyst-free conditions

被引：11

作者：

Zhao, Wei ^{[1
]}

Xuan, Liangming ^{[1
]}

Liu, Yang ^{[1
]}

Yin, Jiayi ^{[1
]}

Wang, Haifeng ^{[1
]}

Yan, Qiongjiao ^{[1
]}

Wang, Wei ^{[1
]}

Huang, Jin ^{[2
]}

Chen, Fener ^{[1
,3
,4
]}

机构：

[1] Wuhan Inst Technol, Pharmaceut Res Inst, Wuhan 430205, Peoples R China

[2] Coll Post & Telecommun WIT, Wuhan 430073, Peoples R China

[3] Fudan Univ, Engn Ctr Catalysis & Synth Chiral Mol, Dept Chem, Shanghai 200433, Peoples R China

[4] Shanghai Engn Ctr Ind Catalysis Chiral Drugs, Shanghai 200433, Peoples R China

来源：

NEW JOURNAL OF CHEMISTRY | 2023年 / 47卷 / 22期

基金：

中国国家自然科学基金;

关键词：

ARYL ACYL PEROXIDES; GAMMA-LACTAMS; AMINODIFLUOROALKYLATION; HETEROCYCLES; QUINOXALINONES; DERIVATIVES; CYCLIZATION; INHIBITORS; CHEMISTRY; ARYLATION;

D O I：

10.1039/d3nj01329d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A visible-light-promoted tandem radical intramolecular 5-exo-trig cyclization/heteroarylation between N-allyl-2-bromo-2,2-difluoroacetamides and quinoxalin-2(1H)-ones or coumarins has been developed without an external photocatalyst. By applying this new approach, a broad range of valuable alpha,alpha-difluoro-gamma-lactam-fused quinoxalin-2(1H)-ones and coumarins (49 examples) can be facilely obtained at room temperature, thus showing the wide utility of this protocol. Moreover, mechanistic experiments reveal the involvement of an electron donor-acceptor (EDA) complex in this transformation.

引用

页码：10744 / 10750

页数：7

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