Literature DB >> 18076177

Highly chemoselective metal-free reduction of tertiary amides.

Guillaume Barbe1, André B Charette.   

Abstract

This communication describes the chemoselective metal-free reduction of tertiary amides to the corresponding amines. Hantzsch ester is used as a mild reducing agent for the reduction of trifluoromethanesulfonic anhydride activated amides providing the tertiary amines with high functional group tolerance.

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Year:  2007        PMID: 18076177     DOI: 10.1021/ja077463q

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  20 in total

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Journal:  J Am Chem Soc       Date:  2019-09-16       Impact factor: 15.419

2.  Cross-coupling of mesylated phenol derivatives with potassium ammonio- and amidomethyltrifluoroborates.

Authors:  Gary A Molander; Floriane Beaumard
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3.  Direct Observation of Intermediates Involved in the Interruption of the Bischler-Napieralski Reaction.

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4.  Chemoselective synthesis of ketones and ketimines by addition of organometallic reagents to secondary amides.

Authors:  William S Bechara; Guillaume Pelletier; André B Charette
Journal:  Nat Chem       Date:  2012-02-21       Impact factor: 24.427

5.  Concise and enantioselective total synthesis of (-)-mehranine, (-)-methylenebismehranine, and related Aspidosperma alkaloids.

Authors:  Marius Mewald; Jonathan William Medley; Mohammad Movassaghi
Journal:  Angew Chem Int Ed Engl       Date:  2014-09-04       Impact factor: 15.336

6.  Uniting Amide Synthesis and Activation by PIII/PV-Catalyzed Serial Condensation: Three-Component Assembly of 2-Amidopyridines.

Authors:  Jeffrey M Lipshultz; Alexander T Radosevich
Journal:  J Am Chem Soc       Date:  2021-09-03       Impact factor: 16.383

7.  Uncovering the importance of proton donors in TmI2-promoted electron transfer: facile C-N bond cleavage in unactivated amides.

Authors:  Michal Szostak; Malcolm Spain; David J Procter
Journal:  Angew Chem Int Ed Engl       Date:  2013-06-12       Impact factor: 15.336

8.  Chemo- and Stereoselective Transition-Metal-Free Amination of Amides with Azides.

Authors:  Veronica Tona; Aurélien de la Torre; Mohan Padmanaban; Stefan Ruider; Leticia González; Nuno Maulide
Journal:  J Am Chem Soc       Date:  2016-06-28       Impact factor: 15.419

9.  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

10.  Copper-mediated synthesis of N-alkenyl-α,β-unsaturated nitrones and their conversion to tri- and tetrasubstituted pyridines.

Authors:  Dimitra Kontokosta; Daniel S Mueller; Dong-Liang Mo; Wiktoria H Pace; Rachel A Simpson; Laura L Anderson
Journal:  Beilstein J Org Chem       Date:  2015-11-04       Impact factor: 2.883

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