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Issue 23, 2014
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Semi-catalytic reduction of secondary amides to imines and aldehydes

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Abstract

Secondary amides can be reduced by silane HSiMe2Ph into imines and aldehydes by a two-stage process involving prior conversion of amides into iminoyl chlorides followed by catalytic reduction mediated by the ruthenium complex [Cp(i-Pr3P)Ru(NCCH3)2]PF6 (1). Alkyl and aryl amides bearing halogen, ketone, and ester groups were converted with moderate to good yields under mild reaction conditions to the corresponding imines and aldehydes. This procedure does not work for substrates bearing the nitro-group and fails for heteroaromatic amides. In the case of cyano substituted amides, the cyano group is reduced to imine.

Graphical abstract: Semi-catalytic reduction of secondary amides to imines and aldehydes

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Publication details

The article was received on 05 Feb 2014, accepted on 25 Apr 2014 and first published on 06 May 2014


Article type: Paper
DOI: 10.1039/C4DT00372A
Author version available: Download Author version (PDF)
Citation: Dalton Trans., 2014,43, 8888-8893
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    Semi-catalytic reduction of secondary amides to imines and aldehydes

    S. Lee and G. I. Nikonov, Dalton Trans., 2014, 43, 8888
    DOI: 10.1039/C4DT00372A

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