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Rhodium(III)‐Catalyzed Enantioselective Coupling of Indoles and 7‐Azabenzonorbornadienes by C−H Activation/Desymmetrization
Author(s) -
Yang Xifa,
Zheng Guangfan,
Li Xingwei
Publication year - 2019
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.201811998
Subject(s) - desymmetrization , enantioselective synthesis , rhodium , catalysis , cyclopentadienyl complex , chemistry , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry
Chiral rhodium(III) cyclopentadienyl catalysts (Cp X Rh III ) play significant roles in asymmetric arene C−H activation. Rh/Ir‐catalyzed couplings of arenes and strained rings have been well‐studied, but they have been limited to racemic systems. Reported in this work is the Cp x Rh III /AgSbF 6 ‐catalyzed enantioselective desymmetrizative C−C coupling of N ‐pyrimidylindoles and 7‐azabenzonorbornadienes with high efficiency and enantioselectivity. The role of AgSbF 6 has been established by mechanistic studies. AgSbF 6 enhances the catalytic activity by suppressing the C3−H activation of the indoles, activation which would otherwise lead to catalytically inactive species.