Inspired by previous studies on synthesizing benzylic boronates through base-catalyzed silaboration or 1,2-diboration of aromatic alkenes, we therefore envisioned that combining these methods with the aforementioned C-B bond activation strategy and classical nucleophilic reactions would offer a valuable method for difunctionalization of alkenes, as well as for a divergent formation of both C-C and C-X bonds. Indeed, the addition of 2.0 equivalents of t BuOK and aryl electrophile 4-cyanopyridine 3a, sequentially, to the resulting mixture of silaboration reaction of styrene 1a under ambient temperature, produced the corresponding carbosilylation product 4 in 85% yield within 30 minutes (Fig. ). However, when 1.0 equivalent of t BuOK was used, the difuntionalization process only produced 4 in 50% yield. Our DFT calculations revealed that the deborylative cross-coupling reaction, involving two molecules of t BuOK, has a much lower activation barrier (11.7 kcal/mol) compared to the pathway with only one molecule of t BuOK (19.9