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

TETRAHEDRON

卷:70

Article

Bantreil, Xavier¹  Kanfar, Nasreddine¹  Gehin, Nicolas¹  Golliard, Ethan¹  Ohlmann, Pauline¹  Martinez, Jean¹  Lamaty, Frederic¹ 

[1] Univ Montpellier 2, ENSCM, Inst Biomol Max Mousseron, UMR 5247,CNRS,UM 1, F-34095 Montpellier 5, France

关键词: Iron;    Homogeneous catalysis;    Amides;    Oxidation;    Green chemistry;   

DOI  :  10.1016/j.tet.2014.06.001

来源: Elsevier

【 摘 要 】

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.

【 授权许可】

Free