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

Author:
Ruan, Zhixiong, Huang, Zhixing, Xu, Zhongnan, Mo, Guangquan, Tian, Xu, Yu, Xi-Yong, Ackermann, Lutz
Source:
Organic letters 2019 v.21 no.4 pp. 1237-1240
ISSN:
1523-7052
Subject:
acrylamides, chemical reactions, electrochemistry, electrolysis, moieties, quinolones, sodium
Abstract:
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.
Agid:
6310532