We initiated our research by investigating the cross-coupling of commercially-available triethyl borane 1a with methyl 4-bromobenzoate 2a to yield alkyl arene 3. Through a preliminary screening of various photocatalysts (Table , Entries 1-3) under blue light irradiation (λ = 456 nm), we discovered that the organic photocatalyst 4CzIPN outperformed the benchmark Ir-based photocatalyst used in previous reports on light-mediated B-alkyl SMC reactions. In contrast, the highly oxidizing acridinium photocatalyst did not prove as effective (Table , Entry 3). Notably, even under non-dry conditions (Table , Entry 4), we obtained product 3 with only a slight reduction in yield, which demonstrates the robustness of the protocol. Diminished yields were observed when using a sub-stoichiometric amount of the base or lower amounts of the alkyl borane (Table , Entries 5 and 6 , underscoring the significance of the base for efficient catalysis and confirming that only one of the alkyl groups transfers to nickel.