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Synfacts 2010(5): 0577-0577  
DOI: 10.1055/s-0029-1219658
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Zinc(II)-Catalyzed Chemoselective Reduction of Amides to Amines

Contributor(s):Paul Knochel, Andrei Gavryushin
S. Das, D. Addis, S. Zhou, K. Junge, M. Beller*
Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Germany
Zinc-Catalyzed Reduction of Amides: Unprecedented Selectivity and Functional Group Tolerance
J. Am. Chem. Soc.  2010,  132:  1770-1771  
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Publication History

Publication Date:
22 April 2010 (online)

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Key words

amide reduction - silanes - zinc

Significance

The catalytic reduction of amides to amines is a highly desirable transformation in organic synthesis. For the first time, an efficient ­reduction of tertiary amides with unprecedented chemoselectivity and unique tolerance to functional groups is reported. Amides can be selectively reduced in excellent yields in the presence of ester, nitro, cyano, azo substituents, or even a ­ketone.

Comment

The role of zinc acetate is not the activation of the amide carbonyl, but rather the activation of the silane with the formation of a complex hydride species. All kinds of tertiary amides can be successfully reduced. For benzamides the reac­tion rate increases when electron-withdrawing groups are present. Some other silanes, such as (EtO)2MeSiH and Ph2SiH2, can also be used.

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