Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 11, Pages 5365-5368Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo500734z
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- NSERC
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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 F-18-trifluoroborate radioprosthetics.
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