Literature DB >> 25815605

Iridium-catalyzed chemoselective reductive nucleophilic addition to N-methoxyamides.

Minami Nakajima1, Takaaki Sato1, Noritaka Chida1.   

Abstract

Iridium-catalyzed reductive nucleophilic addition to N-methoxyamides is reported. The reaction took place in high yields in the presence of a variety of sensitive functional groups such as esters and nitro groups. Mechanistic studies revealed that the reaction of N-methoxyamides proceeded without equilibrium to an enamine intermediate in contrast to that with tert-amides.

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Year:  2015        PMID: 25815605     DOI: 10.1021/acs.orglett.5b00664

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  7 in total

1.  Activation of C-O and C-N Bonds Using Non-Precious-Metal Catalysis.

Authors:  Timothy B Boit; Ana S Bulger; Jacob E Dander; Neil K Garg
Journal:  ACS Catal       Date:  2020-09-10       Impact factor: 13.084

2.  Difluoroalkylation of Tertiary Amides and Lactams by an Iridium-Catalyzed Reductive Reformatsky Reaction.

Authors:  Phillip Biallas; Ken Yamazaki; Darren J Dixon
Journal:  Org Lett       Date:  2022-03-08       Impact factor: 6.072

3.  Mild Reductive Functionalization of Amides into N-Sulfonylformamidines.

Authors:  Paz Trillo; Tove Slagbrand; Fredrik Tinnis; Hans Adolfsson
Journal:  ChemistryOpen       Date:  2017-07-03       Impact factor: 2.911

4.  Tertiary amine synthesis via reductive coupling of amides with Grignard reagents.

Authors:  Lan-Gui Xie; Darren J Dixon
Journal:  Chem Sci       Date:  2017-09-11       Impact factor: 9.825

5.  Iridium-catalyzed reductive Ugi-type reactions of tertiary amides.

Authors:  Lan-Gui Xie; Darren J Dixon
Journal:  Nat Commun       Date:  2018-07-19       Impact factor: 14.919

6.  Iterative addition of carbon nucleophiles to N,N-dialkyl carboxamides for synthesis of α-tertiary amines.

Authors:  Jiahua Chen; Jun Wei Lim; Derek Yiren Ong; Shunsuke Chiba
Journal:  Chem Sci       Date:  2021-11-26       Impact factor: 9.825

7.  A General Iridium-Catalyzed Reductive Dienamine Synthesis Allows a Five-Step Synthesis of Catharanthine via the Elusive Dehydrosecodine.

Authors:  Pablo Gabriel; Yaseen A Almehmadi; Zeng Rong Wong; Darren J Dixon
Journal:  J Am Chem Soc       Date:  2021-07-13       Impact factor: 15.419

  7 in total

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