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Base-promoted protodeboronation of 2,6-disubstituted arylboronic acids}

TitleBase-promoted protodeboronation of 2,6-disubstituted arylboronic acids}
Publication TypeJournal Article
Year of Publication2014
AuthorsLozada, J, Liu, Z, Perrin, DM
JournalJ. Org. Chem.
Volume79
Pagination5365–5368
Date PublishedJun
Abstract

Facile based promoted deboronation of electron-deficient arylboronate esters was observed for arylboronates containing two ortho electron-withdrawing group (EWG) substituents. Among 30 representative boronates, only the diortho-substituted species underwent facile C-B fission in aqueous basic conditions (200 mM hydroxide). These results provide fundamental insight into deboronative mechanisms with implications for cross-coupling reactions, regioselective deuteration/tritiation for isotopic labeling, and the design of new (18)F-trifluoroborate radioprosthetics.