Interestingly, despite their widespread utilization in thermal chemistry, the use of alkyl boranes in photocatalytic reactions has hitherto been overlooked. In this study, we present the convenient utilization of said alkyl boranes as versatile coupling partners, establishing a robust and scalable platform for constructing C(sp 3 )-C(sp 2 ) bonds via Suzuki-Miyaura cross-coupling (SMC), made possible by integrating photocatalysis and nickel catalysis (Scheme 1C). Our protocol specifically caters to the introduction of non-activated alkyl fragments, making it complementary to other metallaphotoredox strategies. The effectiveness of this coupling strategy is exemplified by successfully incorporating complex alkyl fragments derived from natural products. Interestingly, our mechanistic studies reveal a unique activation strategy that operates through polar transmetalation rather than alkyl radical formation, setting it apart from established metallaphotoredox protocols. Additionally, we demonstrate the potential of flow technology in realizing a scalable, safe and streamlined process, combining both the hydroboration and the light-mediated B-alkyl SMC reaction. 21