Literature DB >> 28393450

Copper-Mediated Decarboxylative Coupling of Benzamides with ortho-Nitrobenzoic Acids by Directed C-H Cleavage.

Kazutaka Takamatsu1, Koji Hirano1, Masahiro Miura1.   

Abstract

A copper-mediated decarboxylative coupling of benzamides with ortho-nitrobenzoic acids by 8-aminoquinoline-directed C-H cleavage has been developed. This reaction proceeds smoothly with only a copper salt to produce the corresponding biaryl compounds in good yields. The products can be easily transformed into various nitrogen-containing heterocyclic compounds. Moreover, the combination of copper and a suitable base promotes a decarboxylative C-H arylation and cyclization sequence to deliver phenanthridinone derivatives in one pot.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−H activation; biaryls; copper; decarboxylation; synthetic methods

Year:  2017        PMID: 28393450     DOI: 10.1002/anie.201701918

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  5 in total

Review 1.  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

2.  Cobalt(iii)-catalyzed site-selective C-H amidation of pyridones and isoquinolones.

Authors:  Feng Gao; Xu Han; Chunpu Li; Lingjun Liu; Zhanqing Cong; Hong Liu
Journal:  RSC Adv       Date:  2018-09-21       Impact factor: 3.361

3.  Electrochemical oxidative decarboxylation and 1,2-aryl migration towards the synthesis of 1,2-diaryl ethers.

Authors:  Faxiang Bu; Lijun Lu; Xia Hu; Shengchun Wang; Heng Zhang; Aiwen Lei
Journal:  Chem Sci       Date:  2020-09-02       Impact factor: 9.825

4.  Copper-mediated oxidative C-H/N-H activations with alkynes by removable hydrazides.

Authors:  Feng Xiong; Bo Li; Chenrui Yang; Liang Zou; Wenbo Ma; Linghui Gu; Ruhuai Mei; Lutz Ackermann
Journal:  Beilstein J Org Chem       Date:  2021-07-08       Impact factor: 2.883

5.  Carboxylate-directed C-H allylation with allyl alcohols or ethers.

Authors:  Xiao-Qiang Hu; Zhiyong Hu; A Stefania Trita; Guodong Zhang; Lukas J Gooßen
Journal:  Chem Sci       Date:  2018-05-21       Impact factor: 9.825

  5 in total

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