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

Aurélien Chardon 1 Tharwat Mohy el dine 1 Rémi Legay 1 Michaël de Paolis 2 Jacques Rouden 1 Jérôme Blanchet 1
1 LCMT - Laboratoire de chimie moléculaire et thioorganique
2 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
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.
Keywords : amides amines reduction organocatalysis borinic acid
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Journal articles
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https://hal-normandie-univ.archives-ouvertes.fr/hal-01793130
Contributor : Jérôme Blanchet <>
Submitted on : Wednesday, May 16, 2018 - 11:22:02 AM
Last modification on : Wednesday, July 1, 2020 - 12:44:30 PM

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COMUE-NORMANDIE | CNRS | ENSICAEN | INSA-ROUEN | INC-CNRS | UNIROUEN | UNICAEN | LCMT | COBRA | INSA-GROUPE | UNILEHAVRE

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Aurélien Chardon, Tharwat Mohy el dine, Rémi Legay, Michaël de Paolis, Jacques Rouden, et al.. Borinic Acid Catalysed Reduction of Tertiary Amides with Hydrosilanes: A Mild and Chemoselective Synthesis of Amines. Chemistry - A European Journal, Wiley-VCH Verlag, 2017, 23 (9), pp.2005-2009. ⟨10.1002/chem.201604802⟩. ⟨hal-01793130⟩

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