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Electrosynthesis of Dihydropyrano[4,3‐ b ]indoles Based on a Double Oxidative [3+3] Cycloaddition
Author(s) -
Choi Subin,
Park Jinhwi,
Yu Eunsoo,
Sim Jeongwoo,
Park CheolMin
Publication year - 2020
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.202003364
Subject(s) - electrosynthesis , chemistry , cycloaddition , tandem , ring (chemistry) , electrochemistry , oxidative coupling of methane , methylene , oxidative phosphorylation , radical cyclization , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , electrode , materials science , biochemistry , composite material
Oxidative [3+3] cycloadditions offer an efficient route for six‐membered‐ring formation. This approach has been realized based on an electrochemical oxidative coupling of indoles/enamines with active methylene compounds followed by tandem 6π‐electrocyclization leading to the synthesis of dihydropyrano[4,3‐ b ]indoles and 2,3‐dihydrofurans. The radical–radical cross‐coupling of the radical species generated by anodic oxidation combined with the cathodic generation of the base from O 2 allows for mild reaction conditions for the synthesis of structurally complex heterocycles.