Literature DB >> 28447458

Nickel-Catalyzed Directed C6-Selective C-H Alkylation of 2-Pyridones with Dienes and Activated Alkenes.

Wataru Miura1, Koji Hirano1, Masahiro Miura1.   

Abstract

A pyridine-directed, C6-selective nickel-catalyzed ring-contracting C-H alkylation of 2-pyridones with 1,5-cyclooctadiene (cod) has been developed. The reaction proceeds smoothly under external-ligand-free conditions and is accelerated uniquely by a K3PO4 base. Preliminary mechanistic investigations with deuterium-labeled substrates and related reactions with some alkenes are also disclosed.

Entities:  

Year:  2017        PMID： 28447458     DOI： 10.1021/acs.joc.7b00682

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


  6 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

Review 2.  A lesson for site-selective C-H functionalization on 2-pyridones: radical, organometallic, directing group and steric controls.

Authors:  Koji Hirano; Masahiro Miura
Journal:  Chem Sci       Date:  2017-11-27       Impact factor: 9.825

3.  Rhodium-catalyzed C-H functionalization of heteroarenes using indoleBX hypervalent iodine reagents.

Authors:  Erwann Grenet; Ashis Das; Paola Caramenti; Jérôme Waser
Journal:  Beilstein J Org Chem       Date:  2018-05-25       Impact factor: 2.883

4.  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

5.  Ru(ii)-catalyzed C6-selective C-H acylmethylation of pyridones using sulfoxonium ylides as carbene precursors.

Authors:  Yangjie Fu; Zhaohui Wang; Qiyu Zhang; Zhiyu Li; Hong Liu; Xiaoling Bi; Jiang Wang
Journal:  RSC Adv       Date:  2020-02-11       Impact factor: 4.036

6.  Rhodium(i)-catalyzed C6-selective C-H alkenylation and polyenylation of 2-pyridones with alkenyl and conjugated polyenyl carboxylic acids.

Authors:  Haoqiang Zhao; Xin Xu; Zhenli Luo; Lei Cao; Bohan Li; Huanrong Li; Lijin Xu; Qinghua Fan; Patrick J Walsh
Journal:  Chem Sci       Date:  2019-09-09       Impact factor: 9.825
  6 in total

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