Borinic Acid Catalysed Reduction of Tertiary Amides with Hydrosilanes: A Mild and Chemoselective Synthesis of Amines. Issue 9 (23rd January 2017)

• Record Type: Journal Article
• Authors: Chardon, Aurélien; Mohy El Dine, Tharwat; Legay, Rémi; De Paolis, Michaël; Rouden, Jacques; Blanchet, Jérôme
• Is Part Of: Chemistry. Volume 23:Issue 9(2017)
• Page Start: 2005
• Page End: 2009
• Publication Date: 2017-01-23
• Subjects: amides -- amines -- borinic acid -- organocatalysis -- reduction; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201604802
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: A reduction of various aryl, alkyl, and α, β‐unsaturated amides with phenylsilane, catalysed by a borinic acid, is reported. The unprecedented reaction was carried out under very mild conditions and led to useful amines. Furthermore, the reaction tolerates a variety of functional groups. Initial investigations implicated that an intermediate diarylhydroborane is involved in the reaction mechanism. Abstract : Unexpected reactivity : The boronic acid‐catalysed reduction of tertiary amides with the use of hydrosilanes efficiently and chemoselectively led to the formation of several useful amines under very mild conditions. The procedure tolerates a variety of functional groups and may become a strong alternative to metal‐ and perfluoroborane‐based reactions.