Organoboronates are a valuable class of building blocks in modern synthesis due to their divergent reactivity, ease of handling, and broad accessibility. The activation of the C-B bond is one of the most critical steps in cross-coupling reactions of organoboronates, and it can be achieved through classical transmetalation reactions at the transition metal center. Recently, the base-mediated strategy has also emerged as versatile tool for C-B bond activation, involving the thermodynamically favorable formation of base-boronate complex (I). In some cases, the ate complex could undergo reversible cleavage of the C-B bond to form carbanion (II, Fig. ). The resulting ate complex or carbanion can ultimately react with electrophiles to form C-C or C-X bonds (X = Si, Ge, Sn, S, Se) (Fig. ). For example, Aggarwal et al. achieved impressive stereospecific coupling of organoboronates with different types of alkyl and heteroatom electrophiles using organolithium/boronate combinations. Similarly, the groups of Morken, Chirik, and Meek demonstrated that alkoxides can promote the C-C coupling reaction of geminal boronates with alkyl halides and carbonyl derivatives. Our particular interest lies in the basemediated activation of benzylic organoboronates, as their coupling with aryl (pseudo)halides can produce highly valuable 1,1-diaryl alkanes, which are key pharmacophores in marketed drugs. Note that Ohmiya recently reported an alkoxide-mediated cross-coupling of tertiary benzylic organoboronates with alkyl or aryl electrophiles, but attempts to extend this procedure to secondary benzylic organoboronates were unsuccessful. Therefore, there is a continued need for approaches to expand the scope of base-promoted cross-coupling reactions involving benzylic organoboronates.