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Amidation Reactions from the Direct Coupling of Metal Carboxylate Salts with Amines

Jordan D. Goodreid, Petar A. Duspara, Caroline Bosch and Robert A. Batey*

*Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, Canada, M5S 3H6, Email: rbateychem.utoronto.ca

J. D. Goodreid, P. A. Duspara, C. Bosch, R. A. Batey, J. Org. Chem., 2014, 79, 943-954.

DOI: 10.1021/jo402374c (free Supporting Information)


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Abstract

An efficient amidation of carboxylate salts with either free amines or their ammonium hydrochloride salts can be achieved in very good yields using HBTU in combination with Hünig’s base in 1-2 h. The protocol is valuable for the coupling of carboxylates for which the corresponding carboxylic acids or acyl chlorides are unstable. Addition of carbon dioxide to a lithiated terminal alkyne enables the synthesis of acetylenic amides in one pot.

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Key Words

amides


ID: J42-Y2014