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Title: Copper-catalyzed oxidative amidation of aldehydes with amine salts: Synthesis of primary, secondary, and tertiary amides
Authors: Ghosh, S.C.
Ngiam, J.S.Y.
Seayad, A.M.
Tuan, D.T.
Chai, C.L.L. 
Chen, A.
Issue Date: 21-Sep-2012
Citation: Ghosh, S.C., Ngiam, J.S.Y., Seayad, A.M., Tuan, D.T., Chai, C.L.L., Chen, A. (2012-09-21). Copper-catalyzed oxidative amidation of aldehydes with amine salts: Synthesis of primary, secondary, and tertiary amides. Journal of Organic Chemistry 77 (18) : 8007-8015. ScholarBank@NUS Repository.
Abstract: A practical method for the amidation of aldehydes with economic ammonium chloride or amine hydrochloride salts has been developed for the synthesis of a wide variety of amides by using inexpensive copper sulfate or copper(I) oxide as a catalyst and aqueous tert-butyl hydroperoxide as an oxidant. This amidation reaction is operationally straightforward and provides primary, secondary, and tertiary amides in good to excellent yields for most cases utilizing inexpensive and readily available reagents under mild conditions. In situ formation of amine salts from free amines extends the substrate scope of the reaction. Chiral amides are also synthesized from their corresponding chiral amines without detectable racemization. The practicality of this amide formation reaction has been demonstrated in an efficient synthesis of the antiarrhythmic drug N-acetylprocainamide. © 2012 American Chemical Society.
Source Title: Journal of Organic Chemistry
ISSN: 00223263
DOI: 10.1021/jo301252c
Appears in Collections:Staff Publications

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