Issue 46, 2018

Chemoselective amide reductions by heteroleptic fluoroaryl boron Lewis acids

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

Supplementary files

Article information

Article type
Communication
Submitted
07 Mar 2018
Accepted
09 May 2018
First published
11 May 2018

Chem. Commun., 2018,54, 5855-5858

Author version available

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, 54, 5855 DOI: 10.1039/C8CC01863D

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