|Title||Base-promoted protodeboronation of 2,6-disubstituted arylboronic acids}|
|Publication Type||Journal Article|
|Year of Publication||2014|
|Authors||Lozada, J, Liu, Z, Perrin, DM|
|Journal||J. Org. Chem.|
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.