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Electrochemical Tri‐ and Difluoromethylation‐Triggered Cyclization Accompanied by the Oxidative Cleavage of Indole Derivatives
Author(s) -
Yuan Xin,
Cui YuSheng,
Zhang XinPeng,
Qin LongZhou,
Sun Qi,
Duan Xiu,
Chen Lin,
Li Guigen,
Qiu JiangKai,
Guo Kai
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202005368
Subject(s) - indole test , isoquinoline , chemistry , oxidative cleavage , reagent , cleavage (geology) , combinatorial chemistry , bond cleavage , oxidative phosphorylation , stereoselectivity , electrochemistry , organic chemistry , catalysis , biochemistry , materials science , electrode , fracture (geology) , composite material
Considering their unique roles in organic synthesis, and pharmaceutical and agrochemical applications, the development of fluoroalkylation, cyclization, and indole oxidative cleavage are important topics. Herein, an unprecedented electrochemical tri‐ and difluoromethylation/cyclization/indole oxidative cleavage process occurring in an undivided cell is presented. The protocol employs a readily prepared Langlois reagent as the fluoroalkyl source, affording a series of tri‐ or difluoromethylated 2‐(2‐acetylphenyl)isoquinoline‐1,3‐diones in good yields with excellent stereoselectivity. It is worth noting that this new methodology merges the fluoroalkylation/cyclization of N‐substituted acrylamide alkenes with the oxidative cleavage of an indole C(2)=C(3) bond under external oxidant‐free conditions.