The ortho-substituent on 2,4-bis(trifluoromethyl)phenylboronic acid catalyzed dehydrative condensation between carboxylic acids and amines

2,4-Bis(trifluoromethyl)phenylboronic acid is a highly effective catalyst for dehydrative amidation between carboxylic acids and amines. Mechanistic studies suggest that a 2 : 2 mixed anhydride is expected to be the only active species, and the ortho-substituent of boronic acid plays a key role in p...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2018, Vol.54 (43), p.5410-5413
Main Authors: Wang, Ke, Lu, Yanhui, Ishihara, Kazuaki
Format: Article
Language:English
Subjects:
Amines
Anhydrides
Boron
Carboxylic acids
Catalysis
Catalysts
Chemical synthesis
Dehydration
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Summary:2,4-Bis(trifluoromethyl)phenylboronic acid is a highly effective catalyst for dehydrative amidation between carboxylic acids and amines. Mechanistic studies suggest that a 2 : 2 mixed anhydride is expected to be the only active species, and the ortho-substituent of boronic acid plays a key role in preventing the coordination of amines to the boron atom of the active species, thus accelerating the amidation. This catalyst works for α-dipeptide synthesis.
ISSN:1359-7345
1364-548X
DOI:10.1039/c8cc02558d