Synthesis of C3-Fluorinated Oxindoles through Reagent-Free Cross-Dehydrogenative Coupling
1iChEM, State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, P.R. China.
Abstract:
Reported herein is an unprecedented synthesis of C3-fluorinated oxindoles through cross-dehydrogenative coupling of C(sp3 )-H and C(sp2 )-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.
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