Literature DB >> 29775290

Manganese-Mediated Reductive Transamidation of Tertiary Amides with Nitroarenes.

Chi Wai Cheung1,2, Jun-An Ma2, Xile Hu1.   

Abstract

Amides are an important class of organic compounds, which have widespread industrial applications. Transamidation of amides is a convenient method to generate new amides from existing ones. Tertiary amides, however, are challenging substrates for transamidation. Here we describe an unconventional approach to the transamidation of tertiary amides using nitroarenes as the nitrogen source under reductive conditions. Manganese metal alone mediates the reactions and no additional catalyst is required. The method exhibits broad scope and high functional group tolerance.

Entities:  

Year:  2018        PMID: 29775290     DOI: 10.1021/jacs.8b03739

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


  9 in total

1.  Chemoselective Transamidation of Thioamides by Transition-Metal-Free N-C(S) Transacylation.

Authors:  Guangchen Li; Yangyang Xing; Hui Zhao; Jin Zhang; Xin Hong; Michal Szostak
Journal:  Angew Chem Int Ed Engl       Date:  2022-02-23       Impact factor: 15.336

2.  Ultrafast amidation of esters using lithium amides under aerobic ambient temperature conditions in sustainable solvents.

Authors:  Michael Fairley; Leonie J Bole; Florian F Mulks; Laura Main; Alan R Kennedy; Charles T O'Hara; Joaquín García-Alvarez; Eva Hevia
Journal:  Chem Sci       Date:  2020-04-30       Impact factor: 9.825

Review 3.  Direct Transamidation Reactions: Mechanism and Recent Advances.

Authors:  Paola Acosta-Guzmán; Alejandra Mateus-Gómez; Diego Gamba-Sánchez
Journal:  Molecules       Date:  2018-09-18       Impact factor: 4.411

4.  SET activation of nitroarenes by 2-azaallyl anions as a straightforward access to 2,5-dihydro-1,2,4-oxadiazoles.

Authors:  Dong Zou; Lishe Gan; Fan Yang; Huan Wang; Youge Pu; Jie Li; Patrick J Walsh
Journal:  Nat Commun       Date:  2021-12-03       Impact factor: 14.919

5.  Fe-mediated synthesis of N-aryl amides from nitroarenes and acyl chlorides.

Authors:  Yundong Wu; Lei Guo; Yuxuan Liu; Jiannan Xiang; Jun Jiang
Journal:  RSC Adv       Date:  2021-04-23       Impact factor: 3.361

6.  A one pot protocol to convert nitro-arenes into N-aryl amides.

Authors:  Elisabetta Massolo; Margherita Pirola; Alessandra Puglisi; Sergio Rossi; Maurizio Benaglia
Journal:  RSC Adv       Date:  2020-01-23       Impact factor: 4.036

7.  Decarboxylative tandem C-N coupling with nitroarenes via SH2 mechanism.

Authors:  Shuaishuai Wang; Tingrui Li; Chengyihan Gu; Jie Han; Chuan-Gang Zhao; Chengjian Zhu; Hairen Tan; Jin Xie
Journal:  Nat Commun       Date:  2022-05-04       Impact factor: 14.919

8.  Photomediated reductive coupling of nitroarenes with aldehydes for amide synthesis.

Authors:  Qingyao Li; Peng Dai; Haidi Tang; Muliang Zhang; Jie Wu
Journal:  Chem Sci       Date:  2022-08-03       Impact factor: 9.969

9.  Efficient cleavage of tertiary amide bonds via radical-polar crossover using a copper(ii) bromide/Selectfluor hybrid system.

Authors:  Zhe Wang; Akira Matsumoto; Keiji Maruoka
Journal:  Chem Sci       Date:  2020-10-14       Impact factor: 9.825

  9 in total

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