Enantioselective Cobalt(III)‐Catalyzed C−H Activation Enabled by Chiral Carboxylic Acid Cooperation

The enantioselective cobalt(III)‐catalyzed C−H alkylation was achieved through the design of a novel chiral acid. The cobalt(III)‐catalyzed enantioselective C−H activation was characterized by high position‐, regio‐ and enantio‐control under exceedingly mild reaction conditions. Thereby, the robust...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2018-11, Vol.57 (47), p.15425-15429
Main Authors: Pesciaioli, Fabio, Dhawa, Uttam, Oliveira, João C. A., Yin, Rongxin, John, Michael, Ackermann, Lutz
Format: Article
Language:English
Subjects:
Activation
Alkylation
asymmetric catalysis
Carboxylic acids
Catalysis
chiral acid
Cobalt
C−H activation
Enantiomers
Functional groups
Kinetics
Reaction kinetics
reaction mechanism
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Summary:The enantioselective cobalt(III)‐catalyzed C−H alkylation was achieved through the design of a novel chiral acid. The cobalt(III)‐catalyzed enantioselective C−H activation was characterized by high position‐, regio‐ and enantio‐control under exceedingly mild reaction conditions. Thereby, the robust cooperative cobalt(III) catalysis proved tolerant of valuable electrophilic functional groups, including hydroxyl, bromo, and iodo substituents. Mechanistic studies revealed a considerable additive effect on kinetics and on a negative non‐linear‐effect. CoIII goes chiral: Enantioselective Cp*CoIII‐catalyzed C−H functionalization was realized by synergistic cooperation with a newly developed chiral carboxylic acid for robust and versatile C−H activation.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201808595