Borinic Acid Catalysed Reduction of Tertiary Amides with Hydrosilanes: A Mild and Chemoselective Synthesis of Amines

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 inve...

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Bibliographic Details
Published in:Chemistry : a European journal 2017-02, Vol.23 (9), p.2005-2009
Main Authors: Chardon, Aurélien, Mohy El Dine, Tharwat, Legay, Rémi, De Paolis, Michaël, Rouden, Jacques, Blanchet, Jérôme
Format: Article
Language:English
Subjects:
Amides
Amines
Aromatic compounds
borinic acid
Chemical Sciences
Chemistry
Formations
Functional groups
Organic chemistry
organocatalysis
Reduction
Reduction (metal working)
Synthesis (chemistry)
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Summary: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. 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.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201604802