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- W2539894319 endingPage "1559" @default.
- W2539894319 startingPage "1551" @default.
- W2539894319 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." @default.
- W2539894319 created "2016-11-04" @default.
- W2539894319 creator A5004567326 @default.
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- W2539894319 creator A5062938444 @default.
- W2539894319 creator A5076927759 @default.
- W2539894319 creator A5080908968 @default.
- W2539894319 date "2017-01-01" @default.
- W2539894319 modified "2023-10-06" @default.
- W2539894319 title "Chemoselective oxidation of aryl organoboron systems enabled by boronic acid-selective phase transfer" @default.
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- W2539894319 doi "https://doi.org/10.1039/c6sc04014d" @default.
- W2539894319 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/5452267" @default.
- W2539894319 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/28572912" @default.
- W2539894319 hasPublicationYear "2017" @default.