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Cobalt‐Catalyzed Tandem C−H Activation/C−C Cleavage/C−H Cyclization of Aromatic Amides with Alkylidenecyclopropanes
Author(s) -
Li Mingliang,
Kwong Fuk Yee
Publication year - 2018
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.201801706
Subject(s) - catalysis , tandem , intramolecular force , chemistry , cobalt , bond cleavage , rhodium , cleavage (geology) , medicinal chemistry , chelation , stereochemistry , combinatorial chemistry , organic chemistry , materials science , fracture (geology) , composite material
Abstract A cobalt‐catalyzed chelation‐assisted tandem C−H activation/C−C cleavage/C−H cyclization of aromatic amides with alkylidenecyclopropanes is reported. This process allows the sequential formation of two C−C bonds, which is in sharp contrast to previous reports on using rhodium catalysts for the formation of C−N bonds. Here the inexpensive catalyst system exhibits good functional‐group compatibility and relatively broad substrate scope. The desired products can be easily transformed into polycyclic lactones with m ‐CPBA. Mechanistic studies revealed that the tandem reaction proceeds through a C−H cobaltation, β‐carbon elimination, and intramolecular C−H cobaltation sequence.