The continuous-flow electrosynthesis of 4-(sulfonylmethyl)isoquinoline-1,3(2H,4H)-diones fromN-alkyl-N-methacryloyl benzamides under metal-free and oxidant-free conditions

An efficient and green electrochemical continuous-flow approach has been developed for the synthesis of 4-(sulfonylmethyl)isoquinoline-1,3(2H,4H)-diones through the sulfonylation of alkenes with sulfonylhydrazides. The reaction proceeds in a continuous-flow electrolytic cell under metal-free and oxi...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 7; no. 20; pp. 3223 - 3228
Main Authors Xu, Jia, Yang, Zhao, Hua, Jiawei, Lin, Yang, Bian, Mixue, Li, Yuguang, Liu, Chengkou, He, Wei, Fang, Zheng, Guo, Kai
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.10.2020
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALCOHOLS
POTENT
SULFONYLATION
SELECTIVE INHIBITORS
OXINDOLES
C-H FUNCTIONALIZATION
DERIVATIVES
CYCLIZATION
DISCOVERY
STRATEGIES
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Summary:An efficient and green electrochemical continuous-flow approach has been developed for the synthesis of 4-(sulfonylmethyl)isoquinoline-1,3(2H,4H)-diones through the sulfonylation of alkenes with sulfonylhydrazides. The reaction proceeds in a continuous-flow electrolytic cell under metal-free and oxidant-free conditions. A series of activated alkenes were suitable for this system, and the corresponding products were obtained in moderate to good yields. Moreover, reaction scale-up was smoothly achieved using the electrochemical continuous-flow system without changing the reaction conditions.
ISSN:2052-4129
DOI:10.1039/d0qo00909a