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Synfacts 2017; 13(12): 1321
DOI: 10.1055/s-0036-1592021
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Direct Amide Condensation by Using Supported Boronates

Contributor(s):
Yasuhiro Uozumi
,
Shun Ichii
Lu Y. Wang K. Ishihara K. * Nagoya University, Japan
Design of Boronic Acid–Base Complexes as Reusable Homogeneous Catalysts in Dehydrative Condensations between Carboxylic Acids and Amines.

Asian J. Org. Chem. 2017;
6: 1191-1194
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Further Information

Publication History

Publication Date:
17 November 2017 (online)

 
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Key words

ammonium boronates - carboxylic acids - amines - condensation - amides

Significance

Polystyrene resin bound quaternary ammonium boronates 1a–c were prepared by treatment of a commercial anion-exchange resin with the appropriate arylboronic acids (eq. 1). Bo­ronates 1a–c catalyzed the dehydrative condensation of carboxylic acids with amines under azeotropic reflux conditions to give the corresponding amides quantitatively (eq. 2).


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Comment

In the dehydrative condensation of 3-phenylpropanoic acid with benzylamine, catalyst 1b was recovered by decantation and reused nine times without loss of its catalytic activity. 1H NMR spectroscopy studies suggested that free arylboronic acids were released from the resin into the solution during the reaction.


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