Literature DB >> 27148754

Copper(II)-Mediated Intermolecular C(sp(2))-H Amination of Benzamides with Electron-Rich Anilines.

Bijaya Kumar Singh1, Arghya Polley1, Ranjan Jana1.   

Abstract

Despite significant progress, copper-catalyzed/mediated C-H amination reactions with electron-rich anilines remain an unsolved problem due to catalyst deactivation and deleterious side reactions. Herein, we report a copper(II)-mediated C(sp(2))-H amination of benzamides with electronically neutral or electron-rich anilines. A dramatic influence of silver(I) and tetrabutylammonium bromide was observed on the reaction outcome. The present protocol also demonstrates the synthesis of a number of nonsteroidal anti-inflammatory drugs.

Entities:  

Year:  2016        PMID: 27148754     DOI: 10.1021/acs.joc.6b00659

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  5 in total

1.  A directing group switch in copper-catalyzed electrophilic C-H amination/migratory annulation cascade: divergent access to benzimidazolone/benzimidazole.

Authors:  Hasina Mamataj Begam; Shantanu Nandi; Ranjan Jana
Journal:  Chem Sci       Date:  2022-04-14       Impact factor: 9.969

2.  N-Aminopyridinium Ylide-Directed, Copper-Promoted Amination of sp2 C-H Bonds.

Authors:  Se Hun Kwak; Olafs Daugulis
Journal:  J Org Chem       Date:  2019-09-10       Impact factor: 4.354

3.  Molecular basis for the P450-catalyzed C-N bond formation in indolactam biosynthesis.

Authors:  Fei He; Takahiro Mori; Iori Morita; Hitomi Nakamura; Miroslava Alblova; Shotaro Hoshino; Takayoshi Awakawa; Ikuro Abe
Journal:  Nat Chem Biol       Date:  2019-10-21       Impact factor: 15.040

Review 4.  A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

Authors:  Carlo Sambiagio; David Schönbauer; Remi Blieck; Toan Dao-Huy; Gerit Pototschnig; Patricia Schaaf; Thomas Wiesinger; Muhammad Farooq Zia; Joanna Wencel-Delord; Tatiana Besset; Bert U W Maes; Michael Schnürch
Journal:  Chem Soc Rev       Date:  2018-08-28       Impact factor: 54.564

5.  Accelerated Ru-Cu Trinuclear Cooperative C-H Bond Functionalization of Carbazoles: A Kinetic and Computational Investigation.

Authors:  Alexander W Jones; Christian K Rank; Yanik Becker; Christian Malchau; Ignacio Funes-Ardoiz; Feliu Maseras; Frederic W Patureau
Journal:  Chemistry       Date:  2018-09-11       Impact factor: 5.236

  5 in total

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