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Chem Commun (Camb). 2018 Jun 5;54(46):5855-5858. doi: 10.1039/c8cc01863d.

Chemoselective amide reductions by heteroleptic fluoroaryl boron Lewis acids.

Author information

1
Caudill Laboratories, Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA. mgagne@unc.edu.

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.

PMID:
29780984
DOI:
10.1039/c8cc01863d

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