title: 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.
authors: Laboratoire de Chimie Moléculaire et Thio-organique, ENSICAEN, Université de Caen Basse-Normandie, CNRS, 6 Boulevard du Maréchal Juin, 14050 Caen, France.
authors: Tharwat
authors: T
authors: Mohy El Dine
authors: Laboratoire de Chimie Moléculaire et Thio-organique, ENSICAEN, Université de Caen Basse-Normandie, CNRS, 6 Boulevard du Maréchal Juin, 14050 Caen, France.
authors: William
authors: W
authors: Erb
authors: Laboratoire de Chimie Moléculaire et Thio-organique, ENSICAEN, Université de Caen Basse-Normandie, CNRS, 6 Boulevard du Maréchal Juin, 14050 Caen, France.
authors: Yohann
authors: Y
authors: Berhault
authors: Laboratoire de Chimie Moléculaire et Thio-organique, ENSICAEN, Université de Caen Basse-Normandie, CNRS, 6 Boulevard du Maréchal Juin, 14050 Caen, France.
authors: Jacques
authors: J
authors: Rouden
authors: Laboratoire de Chimie Moléculaire et Thio-organique, ENSICAEN, Université de Caen Basse-Normandie, CNRS, 6 Boulevard du Maréchal Juin, 14050 Caen, France.
authors: Jérôme
authors: J
authors: Blanchet
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013696:Temperature
chemical_list: D000577:Amides; D004151:Dipeptides