Chemoselective oxidation of aryl organoboron systems enabled by boronic acid-selective phase transfer was written by Molloy, John J.;Clohessy, Thomas A.;Irving, Craig;Anderson, Niall A.;Lloyd-Jones, Guy C.;Watson, Allan J. B.. And the article was included in Chemical Science in 2017.Electric Literature of C6H7NO2 This article mentions the following:
The authors report the direct chemoselective Brown-type oxidation of aryl organoboron systems containing two oxidizable B 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 equilibrium Spectroscopic studies 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. The authors 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. In the experiment, the researchers used many compounds, for example, 5-Hydroxy-2-methoxylpyridine (cas: 51834-97-0Electric Literature of C6H7NO2).
5-Hydroxy-2-methoxylpyridine (cas: 51834-97-0) belongs to pyridine derivatives. Pyridine’s the lone pair does not contribute to the aromatic system but importantly influences the chemical properties of pyridine, as it easily supports bond formation via an electrophilic attack. Pyridine derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Electric Literature of C6H7NO2