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Palladium‐Catalyzed Site‐Selective [3+2] Annulation via Benzylic and meta C−H Bond Activation
Author(s) -
He Qiyuan,
Chatani Naoto
Publication year - 2021
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.202015054
Subject(s) - annulation , chemistry , palladium , catalysis , bond cleavage , medicinal chemistry , cleavage (geology) , stereochemistry , organic chemistry , materials science , fracture (geology) , composite material
The palladium‐catalyzed [3+2] annulation of aromatic amides with maleimides via the activation of ortho benzylic C−H and meta C−H bonds is reported. Carboxamide and anilide type substrates that contain a 2‐methylthiophenyl group both participate in this [3+2] annulation, indicating that the presence of a 2‐methylthiophenyl directing group is a key for the success of the reaction. The first C−H bond activation at the benzylic C−H bond is followed by a second C−H bond activation at the meta C−H bond to give five‐membered cyclic products. The cleavage of these C−H bonds is irreversible.