Catalyst-Free, Direct Electrochemical Tri- and Difluoroalkylation/Cyclization: Access to Functionalized Oxindoles and Quinolinones

Catalyst-Free, Direct Electrochemical Tri- and Difluoroalkylation/Cyclization: Access to Functionalized Oxindoles and Quinolinones

The catalyst-free electrochemical di- and trifluoromethylation/cyclization of N-substituted acrylamides was realized under external oxidant-free conditions. The strategy provides expedient access to fluoroalkylated oxindoles and 3,4-dihydroquinolin-2­(1H)-ones with ample scope and broad functional g...

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Veröffentlicht in:Organic letters 2019-02, Vol.21 (4), p.1237-1240
Hauptverfasser: Ruan, Zhixiong, Huang, Zhixing, Xu, Zhongnan, Mo, Guangquan, Tian, Xu, Yu, Xi-Yong, Ackermann, Lutz
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container_end_page 1240
container_issue 4
container_start_page 1237
container_title Organic letters
container_volume 21
creator Ruan, Zhixiong
Huang, Zhixing
Xu, Zhongnan
Mo, Guangquan
Tian, Xu
Yu, Xi-Yong
Ackermann, Lutz
description The catalyst-free electrochemical di- and trifluoromethylation/cyclization of N-substituted acrylamides was realized under external oxidant-free conditions. The strategy provides expedient access to fluoroalkylated oxindoles and 3,4-dihydroquinolin-2­(1H)-ones with ample scope and broad functional group tolerance by mild, direct electrolysis of sodium sulfinates in an undivided cell. Detailed mechanistic studies provided strong support for a SET-based reaction manifold.
doi_str_mv 10.1021/acs.orglett.9b00361
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title Catalyst-Free, Direct Electrochemical Tri- and Difluoroalkylation/Cyclization: Access to Functionalized Oxindoles and Quinolinones
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