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Catalytic Chemical Amide Synthesis at Room Temperature: One More Step Toward Peptide Synthesis

Tharwat Mohy El Dine, William Erb, Yohann Berhault, Jacques Rouden and Jérôme Blanchet*

*Laboratoire de Chimie Moléculaire et Thio-organique, ENSICAEN, Université de Caen Basse-Normandie, CNRS, 6 Boulevard du Maréchal Juin, 14050 Caen, France, Email: jerome.blanchetensicaen.fr

T. M. El Dine, W. Erb, Y. Berhault, J. Rouden, J. Blanchet, J. Org. Chem., 2015, 80, 4532-4544.

DOI: 10.1021/acs.joc.5b00378 (free Supporting Information)


 

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Abstract

(2-(Thiophen-2-ylmethyl)phenyl)boronic acid is a a highly active catalyst for direct amidation between carboxylic acids and amines at room temperature for a large range of substrates. Slightly higher temperatures are required for challenging starting materials. Aliphatic, α-hydroxyl, aromatic, and heteroaromatic acids as well as primary, secondary, heterocyclic, and even functionalized amines can be used.

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Key Words

amides


ID: J42-Y2015