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Metal‐Free Radical‐Triggered Selenosulfonation of 1,7‐Enynes for the Rapid Synthesis of 3,4‐Dihydroquinolin‐2(1 H )‐ones in Batch and Flow
Author(s) -
Qiu JiangKai,
Shan Cheng,
Wang DeCai,
Wei Ping,
Jiang Bo,
Tu ShuJiang,
Li Guigen,
Guo Kai
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201701118
Subject(s) - chemistry , combinatorial chemistry , scope (computer science) , continuous flow , computational chemistry , nanotechnology , biochemical engineering , computer science , engineering , materials science , programming language
A novel three‐component selenosulfonation of 1,7‐enynes with sulfinic acids and diphenyl diselenides for the formation of multifunctional 3,4‐dihydroquinolin‐2(1 H )‐ones was developed in batch and flow. This room‐temperature protocol provides a highly efficient approach to diverse selenosulfones in moderate to excellent yields and with a broad scope of substrates. It should provide a potential synthesis method for the construction of diverse and meaningful 3,4‐dihydroquinolin‐2(1 H )‐ones derivatives in the fields of pharmaceutical and biological chemistry. Additionally, an obvious acceleration (20 h to 43 s) was obtained under micro flow conditions.