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Design of Boronic Acid–Base Complexes as Reusable Homogeneous Catalysts in Dehydrative Condensations between Carboxylic Acids and Amines

Design of Boronic Acid–Base Complexes as Reusable Homogeneous Catalysts in Dehydrative... Two novel boronic acid–base complexes were developed as reusable homogeneous catalysts for amide condensation. First, quaternary ammonium resin‐bound boronates were shown to be effective catalysts that might release free boronic acids during reactions and could be regenerated afterwards. Next, a 1:1 mixture of 3,5‐dinitro‐4‐tolueneboronic acid and 4‐(N,N‐dimethylamino)pyridine N‐oxide (DMAPO) or 4‐(N,N,‐dimethylamino)pyridine (DMAP) cooperatively promoted amide formation and precipitated as an acid–base solid complex after cooling. These inexpensive and reusable complexes may be useful in large‐scale process chemistry. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Asian Journal of Organic Chemistry Wiley

Design of Boronic Acid–Base Complexes as Reusable Homogeneous Catalysts in Dehydrative Condensations between Carboxylic Acids and Amines

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References (33)

Publisher
Wiley
Copyright
© 2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
ISSN
2193-5807
eISSN
2193-5815
DOI
10.1002/ajoc.201700194
Publisher site
See Article on Publisher Site

Abstract

Two novel boronic acid–base complexes were developed as reusable homogeneous catalysts for amide condensation. First, quaternary ammonium resin‐bound boronates were shown to be effective catalysts that might release free boronic acids during reactions and could be regenerated afterwards. Next, a 1:1 mixture of 3,5‐dinitro‐4‐tolueneboronic acid and 4‐(N,N‐dimethylamino)pyridine N‐oxide (DMAPO) or 4‐(N,N,‐dimethylamino)pyridine (DMAP) cooperatively promoted amide formation and precipitated as an acid–base solid complex after cooling. These inexpensive and reusable complexes may be useful in large‐scale process chemistry.

Journal

Asian Journal of Organic ChemistryWiley

Published: Sep 1, 2017

Keywords: ; ; ; ;

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