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Issue 13, 2019
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Selective reduction of formamides to O-silylated hemiaminals or methylamines with HSiMe2Ph catalyzed by iridium complexes

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Abstract

The reaction of (4-methyl-pyridin-2-iloxy)ditertbutylsilane (NSitBu–H, 1) with [IrCl(coe)2]2 affords the iridium(III) complex [Ir(H)(Cl)(κ2-NSitBu)(coe)] (2), which has been fully characterized including X-ray diffraction studies. The reaction of 2 with AgCF3SO3 leads to the formation of species [Ir(H)(CF3SO3)(κ2-NSitBu)(coe)] (3). The iridium complexes 2 and 3 are effective catalysts for the reduction of formamides with HSiMe2Ph. The selectivity of the reduction process depends on the catalyst. Thus, by using complex 2, with a chloride ancillary ligand, it has been possible to selectively obtain the corresponding O-silylated hemiaminal by reaction of formamides with one equivalent of HSiMe2Ph, while complex 3, with a triflate ligand instead of chloride, catalyzed the selective reduction of formamides to the corresponding methylamine.

Graphical abstract: Selective reduction of formamides to O-silylated hemiaminals or methylamines with HSiMe2Ph catalyzed by iridium complexes

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Publication details

The article was received on 22 Dec 2018, accepted on 25 Feb 2019 and first published on 26 Feb 2019


Article type: Paper
DOI: 10.1039/C8DT05070H
Dalton Trans., 2019,48, 4255-4262

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    Selective reduction of formamides to O-silylated hemiaminals or methylamines with HSiMe2Ph catalyzed by iridium complexes

    J. Guzmán, A. M. Bernal, P. García-Orduña, F. J. Lahoz, L. A. Oro and F. J. Fernández-Alvarez, Dalton Trans., 2019, 48, 4255
    DOI: 10.1039/C8DT05070H

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