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Chemoselective amide reductions by heteroleptic fluoroaryl boron Lewis acids

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Abstract

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.

Graphical abstract: Chemoselective amide reductions by heteroleptic fluoroaryl boron Lewis acids

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Publication details

The article was received on 07 Mar 2018, accepted on 09 May 2018 and first published on 11 May 2018


Article type: Communication
DOI: 10.1039/C8CC01863D
Citation: Chem. Commun., 2018, Advance Article
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    Chemoselective amide reductions by heteroleptic fluoroaryl boron Lewis acids

    M. T. Peruzzi, Q. Q. Mei, S. J. Lee and M. R. Gagné, Chem. Commun., 2018, Advance Article , DOI: 10.1039/C8CC01863D

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