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
收藏
页码：10744 / 10750
页数：7
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