Base-promoted protodeboronation of 2,6-disubstituted arylboronic acids.
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.
Department of Chemistry, University of British Columbia , Vancouver BC, Canada.
Jerome
J
Lozada
Zhibo
Z
Liu
David M
DM
Perrin