Chemoselective oxidation of aryl organoboron systems enabled by boronic acid-selective phase transfer

Molloy, John J. and Clohessy, Thomas Aidan and Irving, Craig and Anderson, Niall A. and Lloyd-Jones, Guy C. and Watson, Allan J. B. (2016) Chemoselective oxidation of aryl organoboron systems enabled by boronic acid-selective phase transfer. Chemical Science. ISSN 2041-6539 (https://doi.org/10.1039/C6SC04014D)

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Abstract

We report the direct chemoselective Brown-type oxidation of aryl organoboron systems containing two oxidizable boron groups. Basic biphasic reaction conditions enable selective formation and phase transfer of a boronic acid trihydroxyboronate in the presence of boronic acid pinacol (BPin) esters, while avoiding speciation equilibria. Spectroscopic investigations validate a base-promoted phase-selective discrimination of organoboron species. This phenomenon is general across a broad range of organoboron compounds and can also be used to invert conventional protecting group strategies, enabling chemoselective oxidation of BMIDA species over normally more reactive BPin substrates. We also demonstrate the selective oxidation of diboronic acid systems with chemoselectivity predictable a priori. The utility of this method is exemplified through the development of a chemoselective oxidative nucleophile coupling.

ORCID iDs

Molloy, John J. ORCID logoORCID: https://orcid.org/0000-0002-0538-7852, Clohessy, Thomas Aidan ORCID logoORCID: https://orcid.org/0000-0002-1098-8302, Irving, Craig, Anderson, Niall A., Lloyd-Jones, Guy C. and Watson, Allan J. B.;
  • Item type:Article
    ID code:58886
    Dates:
    Date
    Event
    27 October 2016
    Published
    27 October 2016
    Published Online
    25 October 2016
    Accepted
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:29 Nov 2016 15:49
    Last modified:11 Nov 2024 11:34
    URI:https://strathprints.strath.ac.uk/id/eprint/58886
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