Chemoselective amide reductions by heteroleptic fluoroaryl boron Lewis acids

The heteroleptic borane catalyst (C6F5)2B(CH2CH2CH2)BPin is found to hydrosilylatively reduce amides under mild conditions. Simple tertiary amides can be reduced using Me2EtSiH, whereas tertiary benzamides required a more reactive secondary silane, Et2SiH2, for efficient reduction. The catalytic sys...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2018, Vol.54 (46), p.5855-5858
Main Authors: Peruzzi, Michael T, Mei, Qiong Qiong, Lee, Stephen J, Gagné, Michel R
Format: Article
Language:English
Subjects:
Amides
Boron
Catalysis
Reduction
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Summary:The heteroleptic borane catalyst (C6F5)2B(CH2CH2CH2)BPin is found to hydrosilylatively reduce amides under mild conditions. Simple tertiary amides can be reduced using Me2EtSiH, whereas tertiary benzamides required a more reactive secondary silane, Et2SiH2, for efficient reduction. The catalytic system described exhibits exceptional chemoselectivity in the reduction of oligoamides and tolerates functionalities which are prone to reduction under similar conditions.
ISSN:1359-7345
1364-548X
DOI:10.1039/c8cc01863d