4.4 Article

Iron-catalyzed benzamide formation. Application to the synthesis of moclobemide

Journal

TETRAHEDRON
Volume 70, Issue 34, Pages 5093-5099

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2014.06.001

Keywords

Iron; Homogeneous catalysis; Amides; Oxidation; Green chemistry

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A convenient and user-friendly method to yield benzamides from primary and secondary amines and various benzylic alcohols in the presence of a cheap iron salt (FeCl2 center dot 4H(2)O) and tert-butylhydroperoxide (70% in water) as a stoichiometric oxidant is described. Control experiments indicated that this reaction might involve radical species. This method proved to be general, generating a family of 30 benzamides and was applied to the preparative synthesis of anti-anxiety drug moclobemide. (C) 2014 Published by Elsevier Ltd.

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