Chemoselective amide reductions by heteroleptic fluoroaryl boron Lewis acids

Chemical Communications : Chem Comm
Michael T PeruzziMichel R Gagné

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.

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Citations

Nov 13, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Casper M MacaulayLaura Turculet
Dec 25, 2019·Chemical Communications : Chem Comm·Evan A Patrick, Warren E Piers
Jun 8, 2021·Chemical Science·Huaquan Fang, Martin Oestreich

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