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Copper‐Promoted Tandem Radical Reaction of 2‐Oxindoles with Formamides: Facile Synthesis of Unsymmetrical Urea Derivatives
Author(s) -
Chen WeiTing,
Bao WenHui,
Ying WeiWei,
Zhu WenMing,
Liang Hongze,
Wei WenTing
Publication year - 2018
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201800132
Subject(s) - chemistry , formamides , cascade reaction , tandem , radical , domino , bond cleavage , copper , selectivity , combinatorial chemistry , substrate (aquarium) , coupling reaction , urea , ring (chemistry) , medicinal chemistry , photochemistry , organic chemistry , formamide , catalysis , materials science , oceanography , composite material , geology
A convenient copper‐promoted tandem radical reaction of 2‐oxindoles with formamides producing unsymmetrical urea derivatives is described. This radical‐mediated reaction enables the formation of one C=O and one C−N bond through a domino C−O coupling, ring cleavage and C−N coupling process, which features a broad substrate scope and excellent selectivity. In addition, t BuOOH not only acts as the oxidant, but also as the oxygen source. The proposed reaction mechanism is supported by control experiments.