Literature DB >> 19402696

Cu(I)-catalyzed C-H alpha-amination of aryl ketones: direct synthesis of imidazolinones.

Baoguo Zhao1, Haifeng Du, Yian Shi.   

Abstract

This paper describes an alpha-amination process of aryl ketones using CuCl as catalyst and di-tert-butyldiaziridinone as the nitrogen source. A variety of imidazolinone derivatives are prepared in moderate yields under mild conditions. A possible catalytic cycle is proposed for this reaction.

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Year:  2009        PMID： 19402696      PMCID： PMC2704946          DOI： 10.1021/jo9004553

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


  41 in total

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Journal:  J Am Chem Soc       Date:  2007-01-31       Impact factor: 15.419

4.  N-H insertion reactions of primary ureas: the synthesis of highly substituted imidazolones and imidazoles from diazocarbonyls.

Authors:  Sang-Hyeup Lee; Kazuhiro Yoshida; Hana Matsushita; Bruce Clapham; Guido Koch; Jürg Zimmermann; Kim D Janda
Journal:  J Org Chem       Date:  2004-12-10       Impact factor: 4.354

5.  Direct coupling of indoles with carbonyl compounds: short, enantioselective, gram-scale synthetic entry into the hapalindole and fischerindole alkaloid families.

Authors:  Phil S Baran; Jeremy M Richter
Journal:  J Am Chem Soc       Date:  2004-06-23       Impact factor: 15.419

6.  Cu(I)-catalyzed asymmetric diamination of conjugated dienes.

Authors:  Haifeng Du; Baoguo Zhao; Weicheng Yuan; Yian Shi
Journal:  Org Lett       Date:  2008-09-03       Impact factor: 6.005

7.  Toward a synthetically useful stereoselective C-H amination of hydrocarbons.

Authors:  Chungen Liang; Florence Collet; Fabien Robert-Peillard; Paul Müller; Robert H Dodd; Philippe Dauban
Journal:  J Am Chem Soc       Date:  2007-12-12       Impact factor: 15.419

Review 8.  Vicinal diamino functionalities as privileged structural elements in biologically active compounds and exploitation of their synthetic chemistry.

Authors:  S R S Saibabu Kotti; Cody Timmons; Guigen Li
Journal:  Chem Biol Drug Des       Date:  2006-02       Impact factor: 2.817

9.  Catalytic asymmetric allylic and homoallylic diamination of terminal olefins via formal C-H activation.

Authors:  Haifeng Du; Baoguo Zhao; Yian Shi
Journal:  J Am Chem Soc       Date:  2008-06-13       Impact factor: 15.419

10.  Synthesis and biological evaluation of imidazol-2-one derivatives as potential antitumor agents.

Authors:  Na Xue; Xiaochun Yang; Rui Wu; Jing Chen; Qiaojun He; Bo Yang; Xiuyang Lu; Yongzhou Hu
Journal:  Bioorg Med Chem       Date:  2007-11-22       Impact factor: 3.641
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  5 in total

Review 1.  Cross-Coupling of Heteroatomic Electrophiles.

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Journal:  Chem Rev       Date:  2019-06-11       Impact factor: 60.622

2.  Synthesis of enantiomerically enriched imidazolidin-2-ones through asymmetric palladium-catalyzed alkene carboamination reactions.

Authors:  Brett A Hopkins; John P Wolfe
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-31       Impact factor: 15.336

3.  Stereoselective radical amination of electron-deficient C(sp3)-H bonds by Co(II)-based metalloradical catalysis: direct synthesis of α-amino acid derivatives via α-C-H amination.

Authors:  Hongjian Lu; Yang Hu; Huiling Jiang; Lukasz Wojtas; X Peter Zhang
Journal:  Org Lett       Date:  2012-09-21       Impact factor: 6.005

4.  Cu(I)-catalyzed sequential diamination and dehydrogenation of terminal olefins: a facile approach to imidazolinones.

Authors:  Yingguang Zhu; Yian Shi
Journal:  Chemistry       Date:  2014-09-11       Impact factor: 5.236

5.  Catalytic diamination of olefins via N-N bond activation.

Authors:  Yingguang Zhu; Richard G Cornwall; Haifeng Du; Baoguo Zhao; Yian Shi
Journal:  Acc Chem Res       Date:  2014-11-17       Impact factor: 22.384
  5 in total

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