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

Abstract : An efficient method has been developed for direct amide bond synthesis between carboxylic acids and amines via (2-(thiophen-2-ylmethyl)phenyl)boronic acid as a highly active bench-stable catalyst. This catalyst was found to be very effective at room temperature for a large range of substrates with slightly higher temperatures required for challenging ones. This methodology can be applied to aliphatic, α-hydroxyl, aromatic, and heteroaromatic acids as well as primary, secondary, heterocyclic, and even functionalized amines. Notably, N-Boc-protected amino acids were successfully coupled in good yields with very little racemization. An example of catalytic dipeptide synthesis is reported.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-01793141
Contributor : Jérôme Blanchet <>
Submitted on : Wednesday, May 16, 2018 - 11:25:08 AM
Last modification on : Thursday, July 2, 2020 - 3:21:39 AM

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Tharwat Mohy El Dine, William Erb, Yohann Berhault, Jacques Rouden, Jérôme Blanchet. Catalytic Chemical Amide Synthesis at Room Temperature: One More Step Toward Peptide Synthesis. Journal of Organic Chemistry, American Chemical Society, 2015, 80 (9), pp.4532 - 4544. ⟨10.1021/acs.joc.5b00378⟩. ⟨hal-01793141⟩

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