Jump to main content
Jump to site search


New Face of Phenalenyl Based Radical in Transition Metal Free C-H Arylation of Heteroarenes at Room Temperature: Trapping the Radical Initiator via C-C σ Bond Formation

Abstract

Radical mediated transition metal free approach for direct C-H bond functionalization of arenes is considered as a cost effective alternative to the transition metal based catalysis. An organic ligand based radical plays key role by generating an aryl radical which undergoes subsequent functionalization process. The design principle of the present study takes the advantage of a relatively stable odd alternant hydrocarbon based phenalenyl (PLY) radical. In this study, the first transition metal free catalysis for direct C-H arylation of a variety of heteroarenes such as azoles, furan, thiophene and pyridine at room temperature has been reported using a phenalenyl based radical without employing any photoactivation step. This protocol has been successfully applied for gram scale synthesis of core moieties of bioactive molecules. The phenalenyl based radical intermediate has been characterized crystallographically by trapping it via the formation of a C-C σ bond between the phenalenyl radical and solvent based radical species.

Back to tab navigation

Supplementary files

Publication details

The article was received on 14 Jun 2017, accepted on 12 Sep 2017 and first published on 12 Sep 2017


Article type: Edge Article
DOI: 10.1039/C7SC02661G
Citation: Chem. Sci., 2017, Accepted Manuscript
  • Open access: Creative Commons BY license
  •   Request permissions

    New Face of Phenalenyl Based Radical in Transition Metal Free C-H Arylation of Heteroarenes at Room Temperature: Trapping the Radical Initiator via C-C σ Bond Formation

    S. K. Mandal, J. Ahmed, S. P, G. Vijaykumar, A. Jose and M. Raj, Chem. Sci., 2017, Accepted Manuscript , DOI: 10.1039/C7SC02661G

    This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements