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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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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cited_by cdi_FETCH-LOGICAL-c4772-90b43852289171ca882f26416031e4dd039a131be59745d9422d21884eb7b4063
cites cdi_FETCH-LOGICAL-c4772-90b43852289171ca882f26416031e4dd039a131be59745d9422d21884eb7b4063
container_end_page 2009
container_issue 9
container_start_page 2005
container_title Chemistry : a European journal
container_volume 23
creator Chardon, Aurélien
Mohy El Dine, Tharwat
Legay, Rémi
De Paolis, Michaël
Rouden, Jacques
Blanchet, Jérôme
description 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.
doi_str_mv 10.1002/chem.201604802
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1521-3765
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subjects Amides
Amines
Aromatic compounds
borinic acid
Chemical Sciences
Chemistry
Formations
Functional groups
Organic chemistry
organocatalysis
Reduction
Reduction (metal working)
Synthesis (chemistry)
title Borinic Acid Catalysed Reduction of Tertiary Amides with Hydrosilanes: A Mild and Chemoselective Synthesis of Amines
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