Hydrosiloxane-Ti-(OiPr)4 : an efficient system for the reduction of primary amides into primary amines as their hydrochloride salts

Stéphane Laval (1) , Wissam Dayoub (1) , Leyla Pehlivan (1) , Estelle Métay (1) , Alain Favre-Réguillon (2, 1) , Dominique Delbrayelle (3) , Gérard Mignani (4) , Marc Lemaire (5)

1 ICBMS - Institut de Chimie et Biochimie Moléculaires et Supramoléculaires
2 LTCP - Laboratoire de transformations chimiques et pharmaceutiques
3 MINAKEM
4 Rhodia
5 CASYEN - Catalyse Synthèse et Environnement

A simple and useful method for the reduction of primary amides into the corresponding amines using a polymethylhydrosiloxane (PMHS)–Ti(OiPr)4 reducing system is described. Aromatic as well as aliphatic primary amides are reduced in high selectivity and excellent yields. The reduction could proceed via dehydration of the primary amide group into the corresponding nitrile which is then reduced into the corresponding primary amine.

Mots clés: Polymethylhydrosiloxane (PMHS); Amines; Primary amides; Reduction; Titanium

Domaines: Chimie organique

Stéphane Laval, Wissam Dayoub, Leyla Pehlivan, Estelle Métay, Alain Favre-Réguillon, et al.. Hydrosiloxane-Ti-(OiPr)4 : an efficient system for the reduction of primary amides into primary amines as their hydrochloride salts. Tetrahedron Letters, 2011, 52 (32), pp.4072-4075. ⟨10.1016/j.tetlet.2011.05.109⟩. ⟨hal-01168571⟩