Chemoselective Deprotection of Symmetrically Diprotected Resorcinol <i>N</i>-Methyliminodiacetate (MIDA) Boronates Using the MIDA Boronate Moiety as a Blocking Group: Synthesis of Monoprotected Resorcinol MIDA Boronates

A novel protocol for the synthesis of monoprotected resorcinol <i>N</i>-methyliminodiacetate (MIDA) boronates was developed via the chemoselective deprotection of diprotected resorcinol MIDA derivatives with identical protecting groups, utilizing the MIDA boronate moiety as a blocking group for deprotection. This protocol exhibited a broad substrate scope, and the resulting MIDA boronates were readily isolated by simple filtration from the reaction mixture. Furthermore, the utility of this protocol was demonstrated by converting the resulting MIDA boronates into value-added chemicals containing resorcinol scaffolds.