Literature DB >> 21915925

Zinc-catalyzed chemoselective reduction of tertiary and secondary amides to amines.

Shoubhik Das1, Daniele Addis, Kathrin Junge, Matthias Beller.   

Abstract

General and convenient procedures for the catalytic hydrosilylation of secondary and tertiary amides under mild conditions have been developed. In the presence of inexpensive zinc catalysts, tertiary amides are easily reduced by applying monosilanes. Key to success for the reduction of the secondary amides is the use of zinc triflate and disilanes with dual Si-H moieties. The presented hydrosilylations proceed with excellent chemoselectivity in the presence of sensitive ester, nitro, azo, nitrile, olefins, and other functional groups, thus making the method attractive for organic synthesis.
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2011        PMID: 21915925     DOI: 10.1002/chem.201101143

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  6 in total

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4.  Highly chemoselective reduction of amides (primary, secondary, tertiary) to alcohols using SmI2/amine/H2O under mild conditions.

Authors:  Michal Szostak; Malcolm Spain; Andrew J Eberhart; David J Procter
Journal:  J Am Chem Soc       Date:  2014-01-31       Impact factor: 15.419

5.  Platinum-Catalyzed Reduction of DMF by 1,1,3,3-Tetramethyldisiloxane, HMeSi2OSiMe2H: New Intermediates HSiMe2OSiMe2OCH2NMe2 and HSiMe2(OSiMe2)3OCH2NMe2 and Their Further Chemical Reactivity.

Authors:  Jorge L Martinez; Hemant K Sharma; Renzo Arias-Ugarte; Keith H Pannell
Journal:  Organometallics       Date:  2014-06-11       Impact factor: 3.876

6.  Towards a general ruthenium-catalyzed hydrogenation of secondary and tertiary amides to amines.

Authors:  Jose R Cabrero-Antonino; Elisabetta Alberico; Kathrin Junge; Henrik Junge; Matthias Beller
Journal:  Chem Sci       Date:  2016-02-09       Impact factor: 9.825

  6 in total

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