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Photoredox-catalyzed three-component difluorobenzylation of quinoxalin-2(1H)-ones with unactivated vinylarenes and BrCF2CO2Et/HCF2CO2H

  • Lu Shen , Jin-Wei Yuan EMAIL logo , Bing Zhang , Sai-Yi Song , Liang-Ru Yang EMAIL logo , Yong-Mei Xiao , Shou-Ren Zhang EMAIL logo and Ling-Bo Qu
Published/Copyright: February 7, 2023
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Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 78 Issue 5

Abstract

An environmentally friendly strategy for the photo-catalyzed three-component reaction between quinoxalin-2(1H)-ones, vinylarenes, with inexpensive and easily accessible ethyl bromodifluoroacetate/sodium difluoromethanesulfinate is described. This protocol exhibits mild conditions, high efficiency, and excellent functional group tolerance, providing a highly efficient approach for the synthesis of difluorobenzylated quinoxalin-2(1H)-ones by the formation of two carbon-carbon bonds. A radical mechanism is responsible for this three-component transformation.

Keywords: difluorobenzylation; ethyl bromodifluoroacetate; photocatalysis; quinoxalin-2(1H)-ones; radical reaction
Corresponding authors: Jin-Wei Yuan and Liang-Ru Yang, School of Chemistry and Chemical Engineering, Henan University of Technology, Zhengzhou 450001, P. R. China, E-mail: (J.-W. Yuan), (L.-R. Yang); and Shou-Ren Zhang, Henan Key Laboratory of Nanocomposites and Applications, Institute of Nanostructured Functional Materials, Huanghe Science and Technology College, Zhengzhou 450006, P. R. China, E-mail:

Funding source: Innovative Funds Plan of Henan University of Technology

Award Identifier / Grant number: 2020ZKCJ29

Funding source: The special fund project of Zhengzhou basic and applied basic research

Award Identifier / Grant number: ZZSZX202001

Award Identifier / Grant number: ZZSZX202002

  1. Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: This work was supported by the Innovative Funds Plan of Henan University of Technology (No. 2020ZKCJ29) and the special fund project of Zhengzhou basic and applied basic research (ZZSZX202001 and ZZSZX202002).

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Supplementary Material

This article contains supplementary material (https://doi.org/10.1515/znb-2022-0126).

Received: 2022-09-22
Accepted: 2022-12-30
Published Online: 2023-02-07
Published in Print: 2023-05-25

© 2023 Walter de Gruyter GmbH, Berlin/Boston

Articles in the same Issue

  1. Frontmatter
  2. In this issue
  3. Research Articles
  4. Photoredox-catalyzed three-component difluorobenzylation of quinoxalin-2(1H)-ones with unactivated vinylarenes and BrCF2CO2Et/HCF2CO2H
  5. Catalyst-free direct synthesis of indeno[1,2-b]indol-5(4bH)-yl benzimidamides
  6. Crystal structure of three chloridocuprate(I, II) complexes with methylene blue (MB) counterions
  7. Crystal structure, photophysical properties, and DFT calculations of a boron difluoride curcumin complex
  8. The double cluster compound [Nb6Cl14(MeCN)4][Nb6Cl14(pyz)4]·6MeCN (Me: methyl, pyz: pyrazine) with a layered structure resulting from weak intermolecular interactions
  9. Expanding transition metal borate chemistry to include main group elements: high-pressure synthesis and structural relation of β-MgB4O7
  10. Eu2Ru3Si5 and Eu2Ir3Ga5 – first europium compounds with U2Mn3Si5-type structure but different europium valence
  11. Mössbauer-spectroscopic characterization of the stannides Sr2Pd2Sn and Eu2Pd2Sn
  12. Orthoamide und Iminiumsalze, CVIII. Umsetzungen von Orthoamiden der Alkincarbonsäuren mit CH/NH-aciden, tautomeriefähigen Verbindungen
  13. Book Review
  14. Thomas J. Meade (Guest Editor), Astrid Sigel, Helmut Sigel, Eva Freisinger, Roland K. O. Sigel (Series Editors): Molecular Bio-Sensors and the Role of Metal Ions
https://doi.org/10.1515/znb-2022-0126
Keywords for this article
difluorobenzylation; ethyl bromodifluoroacetate; photocatalysis; quinoxalin-2(1H)-ones; radical reaction

Articles in the same Issue

  1. Frontmatter
  2. In this issue
  3. Research Articles
  4. Photoredox-catalyzed three-component difluorobenzylation of quinoxalin-2(1H)-ones with unactivated vinylarenes and BrCF2CO2Et/HCF2CO2H
  5. Catalyst-free direct synthesis of indeno[1,2-b]indol-5(4bH)-yl benzimidamides
  6. Crystal structure of three chloridocuprate(I, II) complexes with methylene blue (MB) counterions
  7. Crystal structure, photophysical properties, and DFT calculations of a boron difluoride curcumin complex
  8. The double cluster compound [Nb6Cl14(MeCN)4][Nb6Cl14(pyz)4]·6MeCN (Me: methyl, pyz: pyrazine) with a layered structure resulting from weak intermolecular interactions
  9. Expanding transition metal borate chemistry to include main group elements: high-pressure synthesis and structural relation of β-MgB4O7
  10. Eu2Ru3Si5 and Eu2Ir3Ga5 – first europium compounds with U2Mn3Si5-type structure but different europium valence
  11. Mössbauer-spectroscopic characterization of the stannides Sr2Pd2Sn and Eu2Pd2Sn
  12. Orthoamide und Iminiumsalze, CVIII. Umsetzungen von Orthoamiden der Alkincarbonsäuren mit CH/NH-aciden, tautomeriefähigen Verbindungen
  13. Book Review
  14. Thomas J. Meade (Guest Editor), Astrid Sigel, Helmut Sigel, Eva Freisinger, Roland K. O. Sigel (Series Editors): Molecular Bio-Sensors and the Role of Metal Ions
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