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Oxidative C−H/C−H Cross‐Coupling Reactions between N ‐Acylanilines and Benzamides Enabled by a Cp*‐Free RhCl 3 /TFA Catalytic System
Author(s) -
Shi Yang,
Zhang Luoqiang,
Lan Jingbo,
Zhang Min,
Zhou Fulin,
Wei Wenlong,
You Jingsong
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201804528
Subject(s) - catalysis , oxidative coupling of methane , chemistry , coupling (piping) , oxidative phosphorylation , medicinal chemistry , organic chemistry , materials science , biochemistry , metallurgy
By making use of a dual‐chelation‐assisted strategy, a completely regiocontrolled oxidative C−H/C−H cross‐coupling reaction between an N ‐acylaniline and a benzamide has been accomplished for the first time. This process constitutes a step‐economic and highly efficient pathway to 2‐amino‐2′‐carboxybiaryl scaffolds from readily available substrates. A Cp*‐free RhCl 3 /TFA catalytic system was developed to replace the [Cp*RhCl 2 ] 2 /AgSbF 6 system generally used in oxidative C−H/C−H cross‐coupling reactions between two (hetero)arenes (Cp*=pentamethylcyclopentadienyl, TFA=trifluoroacetic acid). The RhCl 3 /TFA system avoids the use of the expensive Cp* ligand and AgSbF 6 . As an illustrative example, the procedure developed herein greatly streamlines the total synthesis of the naturally occurring benzo[ c ]phenanthridine alkaloid oxynitidine, which was accomplished in excellent overall yield.