Literature DB >> 26471349

Oxidative C-H Activation Approach to Pyridone and Isoquinolone through an Iron-Catalyzed Coupling of Amides with Alkynes.

Tatsuaki Matsubara1, Laurean Ilies2, Eiichi Nakamura3.   

Abstract

An iron catalyst combined with a mild organic oxidant promotes both C-H bond cleavage and C-N bond formation, and forms 2-pyridones and isoquinolones from an alkene- or arylamide and an internal alkyne, respectively. An unsymmetrical alkyne gives the pyridone derivative with high regioselectivity, this could be due to the sensitivity of the reaction to steric effects because of the compact size of iron.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  2-pyridones; C−H activation; alkynes; amides; iron

Mesh:

Substances:

Year:  2015        PMID: 26471349     DOI: 10.1002/asia.201501095

Source DB:  PubMed          Journal:  Chem Asian J        ISSN: 1861-471X


  8 in total

1.  Nickel-Catalyzed Reduction of Secondary and Tertiary Amides.

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2.  Nickel-Catalyzed Esterification of Aliphatic Amides.

Authors:  Liana Hie; Emma L Baker; Sarah M Anthony; Jean-Nicolas Desrosiers; Chris Senanayake; Neil K Garg
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3.  Additive and Counterion Effects in Iron-Catalyzed Reactions Relevant to C-C Bond Formation.

Authors:  Nikki J Bakas; Michael L Neidig
Journal:  ACS Catal       Date:  2021-06-29       Impact factor: 13.700

4.  Synthesis of highly substituted benzene ring systems through three-component coupling of enyne imines, Fischer carbene complexes, and electron-deficient alkynes.

Authors:  Bishnu Dhakal; Lalith S R Gamage; Yanshi Zhang; James W Herndon
Journal:  Tetrahedron Lett       Date:  2017-02-24       Impact factor: 2.415

Review 5.  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

6.  Co-catalyzed ortho-C-H functionalization/annulation of arenes and alkenes with alkynylsilanes: access to isoquinolone and pyridone motifs.

Authors:  Cong Lin; Liang Shen
Journal:  RSC Adv       Date:  2019-09-26       Impact factor: 4.036

Review 7.  Iron-Catalyzed C-H Functionalizations under Triazole-Assistance.

Authors:  Matteo Lanzi; Gianpiero Cera
Journal:  Molecules       Date:  2020-04-15       Impact factor: 4.411

8.  Divergent rhodium-catalyzed electrochemical vinylic C-H annulation of acrylamides with alkynes.

Authors:  Yi-Kang Xing; Xin-Ran Chen; Qi-Liang Yang; Shuo-Qing Zhang; Hai-Ming Guo; Xin Hong; Tian-Sheng Mei
Journal:  Nat Commun       Date:  2021-02-10       Impact factor: 14.919

  8 in total

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