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Issue 43, 2018
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The ortho-substituent on 2,4-bis(trifluoromethyl)phenylboronic acid catalyzed dehydrative condensation between carboxylic acids and amines

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Abstract

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.

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

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Supplementary files

Article information


Submitted
29 Mar 2018
Accepted
24 Apr 2018
First published
24 Apr 2018

Chem. Commun., 2018,54, 5410-5413
Article type
Communication

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

K. Wang, Y. Lu and K. Ishihara, Chem. Commun., 2018, 54, 5410
DOI: 10.1039/C8CC02558D

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