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Borinic Acid Catalysed Reduction of Tertiary Amides with Hydrosilanes: A Mild and Chemoselective Synthesis of Amines
Author(s) -
Chardon Aurélien,
Mohy El Dine Tharwat,
Legay Rémi,
De Paolis Michaël,
Rouden Jacques,
Blanchet Jérôme
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201604802
Subject(s) - phenylsilane , chemistry , alkyl , reaction conditions , aryl , organic chemistry , reaction mechanism , combinatorial chemistry , medicinal chemistry , catalysis
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.