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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_anqiices.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 (free Supporting Information)


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

Amides, tert-butyl hydroperoxide, aldehydes, copper sulfate


ID: J42-Y2012-3030