Visible-light-induced radical cascade reaction to prepare oxindoles via alkyl radical addition to N-arylacryl amides

被引：7
|
作者：
Cheng, Hanchao [1 ]
Luo, Yunfeng [1 ]
Lam, Tsz-Lung [2 ]
Liu, Yungen [1 ]
Che, Chi-Ming [1 ,2 ,3 ,4 ]
机构：
[1] Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Guangdong, Peoples R China
[2] Univ Hong Kong, Dept Chem, State Key Lab Synthet Chem, Pokfulam Rd, Hong Kong, Peoples R China
[3] HKU Shenzhen Inst Res & Innovat, Shenzhen 518057, Guangdong, Peoples R China
[4] Lab Synthet Chem & Chem Biol Ltd, Units 1503-1511,15-F,Bldg 17W,Hong Kong Sci Pk, Hong Kong, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2022年 / 9卷 / 21期
关键词：
EFFICIENT APPROACH; DIFUNCTIONALIZATION; INSERTION; CYCLIZATION; ISOCYANIDE; ALKENES;
D O I：
10.1039/d2qo01140a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Herein we describe a photochemical approach towards oxindoles by the radical cascade reaction of alpha,beta-unsaturated N-arylacryl amides with alkyl bromides or iodides upon visible light irradiation. This transition metal- and photosensitizer-free protocol afforded diverse oxindoles with C3 quaternary centers in high product yields under mild reaction conditions. Importantly, the method was applicable to prepare the core skeletons of (+/-)-physovenine, (+/-)-esermethole and (+/-)-physostigmine.
引用
收藏
页码：5962 / 5968
页数：7
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