Jump to main content
Jump to site search

Issue 1, 2017
Previous Article Next Article

Unified synthesis of mono/bis-arylated phenols via RhIII-catalyzed dehydrogenative coupling

Author affiliations

Abstract

2,6-Bis-arylated phenols are rarely reported and are synthetically challenging. Directed C–H functionalization reactions, using a directing group (DG), might provide a convenient solution to their synthesis. However, this strategy usually results in partial cleavage of the directing group, preventing further/second C–H activation cascades. Herein we report a general strategy that allows for the precise control of the oxidation pathways so that directing groups can be either preserved or cleaved. We found that N-phenoxyacetamides could undergo ortho-arylation reactions with or without an external oxidant, yielding products with different oxidation states, notably the rare bis-arylated phenols. Notably, a unique rhodacycle intermediate was isolated, characterized by X-ray crystallography, and confirmed to be an active catalyst. Switching between internal and external oxidation could be a general strategy in diverse directed C–H functionalization reactions to realize bis-functionalized products.

Graphical abstract: Unified synthesis of mono/bis-arylated phenols via RhIII-catalyzed dehydrogenative coupling

Back to tab navigation
Please wait while Download options loads

Supplementary files

Publication details

The article was received on 18 Jul 2016, accepted on 02 Aug 2016, published on 03 Aug 2016 and first published online on 03 Aug 2016


Article type: Edge Article
DOI: 10.1039/C6SC03169B
Citation: Chem. Sci., 2017,8, 169-173
  • Open access: Creative Commons BY license
  •   Request permissions

    Unified synthesis of mono/bis-arylated phenols via RhIII-catalyzed dehydrogenative coupling

    Q. Wu, Y. Chen, D. Yan, M. Zhang, Y. Lu, W. Sun and J. Zhao, Chem. Sci., 2017, 8, 169
    DOI: 10.1039/C6SC03169B

    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