Copper-Catalyzed Oxidative Amidation of Aldehydes with Amine Salts: Synthesis of Primary, Secondary, and Tertiary Amides
Subhash Chandra Ghosh, Joyce S. Y. Ngiam, Abdul M. Seayad, Dang Thanh Tuan, Christina L. L. Chai and Anqi Chen*
*Institute of Chemical and Engineering Sciences, Agency for
Science, Technology and Research (A*STAR), 8 Biomedical Grove, Neuros 07-01,
Singapore 138665, Email: chen_anqi
ices.a-star.edu.sg
S. C. Ghosh, J. S. Y. Ngiam, A. M. Seayad, D. T. Tuan, C. L. L. Chai, A. Chen, J. Org. Chem., 2012, 77, 8007-8015.
DOI: 10.1021/jo301252c
Abstract
An operationally straightforward method for the amidation of aldehydes with economic ammonium chloride or amine hydrochloride salts enables the synthesis of various amides in good yield by using inexpensive copper sulfate or copper(I) oxide as a catalyst and aqueous tert-butyl hydroperoxide as an oxidant. Chiral amines can be used without detectable racemization.
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Key Words
oxidative amidation, tert-butyl hydroperoxide, aldehydes, copper sulfate
ID: J42-Y2012-3030
