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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:

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

DOI: 10.1021/jo402374c

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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


ID: J42-Y2014