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- Title
Oxidative C−H/C−H Cross‐Coupling Reactions between N‐Acylanilines and Benzamides Enabled by a Cp*‐Free RhCl<sub>3</sub>/TFA Catalytic System.
- Authors
Shi, Yang; Zhang, Luoqiang; Lan, Jingbo; Zhang, Min; Zhou, Fulin; Wei, Wenlong; You, Jingsong
- Abstract
Abstract: 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 RhCl3/TFA catalytic system was developed to replace the [Cp*RhCl2]2/AgSbF6 system generally used in oxidative C−H/C−H cross‐coupling reactions between two (hetero)arenes (Cp*=pentamethylcyclopentadienyl, TFA=trifluoroacetic acid). The RhCl3/TFA system avoids the use of the expensive Cp* ligand and AgSbF6. 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.
- Subjects
BENZAMIDE; COUPLING reactions (Chemistry); ALKALOIDS
- Publication
Angewandte Chemie, 2018, Vol 130, Issue 29, p9246
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201804528