Synthesis of alpha-Borylated Ketones by Regioselective Wacker Oxidation of Alkenylboronates

As part of a program aimed at metal-catalyzed oxidative transformations of molecules with carbon metalloid bonds, the synthesis of alpha-borylated ketones is reported via regioselective TBHP-mediated Wacker-type oxidation of N-methyliminodiacetic acid (MIDA)-protected alkenylboronates. The observed regioselectivity correlates with the hemilabile nature of the B-N dative bond in the MIDA boronate functional group, which allows boron to guide selectivity through a neighboring group effect.