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Synthesis of C3‐Fluorinated Oxindoles through Reagent‐Free Cross‐Dehydrogenative Coupling
Author(s) -
Wu ZhengJian,
Xu HaiChao
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201701329
Subject(s) - electrolysis , combinatorial chemistry , reagent , electrochemistry , substrate (aquarium) , malonate , chemistry , base (topology) , organic chemistry , electrode , mathematical analysis , oceanography , electrolyte , geology , mathematics
Reported herein is an unprecedented synthesis of C3‐fluorinated oxindoles through cross‐dehydrogenative coupling of C(sp 3 )‐H and C(sp 2 )‐H bonds from malonate amides. Under the unique and mild electrochemical conditions, the requisite oxidant and base are generated in a continuous fashion, allowing the formation of the base‐ and heat‐sensitive 3‐fluorooxindoles in high efficiency with broad substrate scope. The synthetic usefulness of the electrochemical method is further highlighted by its easy scalability and the diverse transformations of the electrolysis product.