Literature DB >> 23640954

Nickel-catalyzed direct alkylation of heterocycles with α-bromo carbonyl compounds: C3-selective functionalization of 2-pyridones.

Akihiro Nakatani1, Koji Hirano, Tetsuya Satoh, Masahiro Miura.   

Abstract

Nickel HAS it: A Ni(cod)2/dppp catalyst system promotes the direct alkylation of electron-rich heterocycles with α-bromo carbonyl compounds and involves an alkyl radical intermediate (see scheme; cod = 1,5-cyclooctadiene, dppp = 1,3-bis(diphenylphosphino)propane). This homolytic radical aromatic substitution (HAS)-type reaction enables the C3-selective direct functionalization of 2-pyridones.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2013        PMID: 23640954     DOI: 10.1002/chem.201301350

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  9 in total

1.  Copper-Catalyzed Alkylation of Nitroalkanes with α-Bromonitriles: Synthesis of β-Cyanonitroalkanes.

Authors:  Kirk W Shimkin; Peter G Gildner; Donald A Watson
Journal:  Org Lett       Date:  2016-02-11       Impact factor: 6.005

2.  Diversity-oriented functionalization of 2-pyridones and uracils.

Authors:  Yong Shang; Chenggui Wu; Qianwen Gao; Chang Liu; Lisha Li; Xinping Zhang; Hong-Gang Cheng; Shanshan Liu; Qianghui Zhou
Journal:  Nat Commun       Date:  2021-05-20       Impact factor: 14.919

3.  Copper-catalyzed direct alkylation of heteroarenes.

Authors:  Cédric Theunissen; Jianjun Wang; Gwilherm Evano
Journal:  Chem Sci       Date:  2017-03-20       Impact factor: 9.825

Review 4.  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

Review 5.  Recent Progress in Nitro-Promoted Direct Functionalization of Pyridones and Quinolones.

Authors:  Feiyue Hao; Nagatoshi Nishiwaki
Journal:  Molecules       Date:  2020-02-05       Impact factor: 4.411

6.  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

7.  The theoretical chemical calculations clarify the mechanism of beta-alkylation of 1-phenylethanol with benzyl alcohol catalyzed by iron(ii) acetylacetonate methods.

Authors:  Wei Feng; Junfeng Zhao; Aiwen Wei; Dandan Zhang; Huiling Liu; Xuri Huang; Kai Sun
Journal:  RSC Adv       Date:  2018-07-03       Impact factor: 3.361

8.  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

9.  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

  9 in total

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