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

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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.

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

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Article information


Submitted
07 Sep 2016
Accepted
25 Oct 2016
First published
27 Oct 2016

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2017,8, 1551-1559
Article type
Edge Article

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

J. J. Molloy, T. A. Clohessy, C. Irving, N. A. Anderson, G. C. Lloyd-Jones and A. J. B. Watson, Chem. Sci., 2017, 8, 1551
DOI: 10.1039/C6SC04014D

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