Literature DB >> 23641707

Assisted tandem catalytic cross metathesis-oxidation: in one flask from styrenes to 1,2-diketones and further to quinoxalines.

Bernd Schmidt1, Stefan Krehl, Sylvia Hauke.   

Abstract

1,2-Diketones were synthesized from styrenes by combining a cross metathesis and a Ru-catalyzed alkene oxidation to an assisted tandem catalytic sequence. The synthesis relies on the use of just one metathesis precatalyst, which was in situ converted to the oxidation catalyst by addition of an alkyl hydroperoxide as a chemical trigger and oxidant. The one-flask sequence can be extended beyond 1,2-diketones to quinoxalines, by condensation of the oxidation products with ortho-phenylenediamine.

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Year:  2013        PMID: 23641707     DOI: 10.1021/jo4005684

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


  5 in total

1.  Sequential Ruthenium Catalysis for Olefin Isomerization and Oxidation: Application to the Synthesis of Unusual Amino Acids.

Authors:  Marc Liniger; Yiyang Liu; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2017-09-25       Impact factor: 15.419

2.  Tandem Z-Selective Cross-Metathesis/Dihydroxylation: Synthesis of anti-1,2-Diols.

Authors:  Peter K Dornan; Zachary K Wickens; Robert H Grubbs
Journal:  Angew Chem Int Ed Engl       Date:  2015-04-27       Impact factor: 15.336

3.  Tandem Olefin Metathesis/Oxidative Cyclization: Synthesis of Tetrahydrofuran Diols from Simple Olefins.

Authors:  Peter K Dornan; Daniel Lee; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2016-05-11       Impact factor: 15.419

4.  I2-Catalyzed Carbonylation of α-Methylene Ketones to Synthesize 1,2-Diaryl Diketones and Antiviral Quinoxalines in One Pot.

Authors:  Lingkai Kong; Jieru Meng; Wenyue Tian; Jiazheng Liu; Xueping Hu; Zhi-Hong Jiang; Wei Zhang; Yanzhong Li; Li-Ping Bai
Journal:  ACS Omega       Date:  2021-12-21

5.  Novel synthesis of divergent aryl imidazoles from ketones involving copper-catalyzed α-amination and oxidative C-C bond cleavage.

Authors:  Jiangkun Huang; Lan Luo; Naiguo Xing; Linghui Gu; Chen Li; Qiao Han; Shilong Zheng; Ling He
Journal:  RSC Adv       Date:  2020-04-06       Impact factor: 4.036

  5 in total

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