Atroposelective sp3 C—H Coupling for Kinetic Resolution of Thioanilide Atropisomers

Main observation and conclusion A highly efficient kinetic resolution of racemic thioanilide atropisomers via C(sp3)−H arylation has been achieved by a hybrid palladium catalyst bearing an anionic chiral CoIII‐complex and a phosphoramidite ligand, leading to both enantioenriched atropisomeric arylat...

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Bibliographic Details
Published in:Chinese journal of chemistry 2021-12, Vol.39 (12), p.3269-3276
Main Authors: Jiang, Hua‐Jie, Geng, Rui‐Long, Wei, Jia‐Hui, Gong, Liu‐Zhu
Format: Article
Language:English
Subjects:
Atropisomerism
Catalysts
Chiral CoIII‐complex
Coordination compounds
C—H activation
Enantiomers
Kinetic resolution
Ligands
Palladium
Phosphoramidite
Substrates
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Summary:Main observation and conclusion A highly efficient kinetic resolution of racemic thioanilide atropisomers via C(sp3)−H arylation has been achieved by a hybrid palladium catalyst bearing an anionic chiral CoIII‐complex and a phosphoramidite ligand, leading to both enantioenriched atropisomeric arylation thioanilides (up to 99% ee) and N‐Me atropisomeric thioanilides (up to 99% ee), simultaneously. The remained enantioenriched substrates can be arylated again by using an achiral anionic ligand to give the enantiomer with the opposite configuration. A C(sp3)–H activation‐based kinetic resolution of racemic thioanilide atropisomers has been developed by using a hybrid palladium catalyst bearing an anionic chiral CoIII‐complex and a phosphoramidite ligand. Both C(sp3)–H arylation atropisomeric thioanilides and remaining starting materials could be accessed with excellent enantioselectivities, simultaneously.
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.202100466