The growing interest in metallaphotoredox approaches for C(sp 2 )-C(sp ) bond formation stems partly from the ability to photochemically generate unstabilized C(sp )-radicals from readily accessible precursors in a reliable and controlled manner. These systems take advantage of mild reaction conditions, enabling the catalytic generation of nucleophilic alkyl radicals, which can then be selectively coupled with C(sp 2 )-electrophiles in the presence of earth-abundant transition metals such as nickel (Scheme 1A i). Our group has recently explored the use of trialkylboranes as radical precursors in metallaphotoredox catalysis. Given that alkyl boranes can be readily synthesized via the venerable Brown hydroboration, a wide range of primary alkyl fragments could be introduced through light-mediated B-alkyl Suzuki-Miyaura coupling. However, incorporating one of the simplest and most ubiquitous alkyl groups-the methyl group-proved challenging. Trimethylborane, a pyrophoric and gaseous reagent, is difficult to obtain and handle safely. While alternative methyl boron sources exist, none have provided a broadly applicable synthetic method for methyl group incorporation in our hands (See Scheme 2). This limitation is of particular significance to medicinal chemistry, where methods for efficient methylation are highly sought after due to the so-called 'magic methyl effect' -a phenomenon in which strategic methylation can dramatically enhance a molecule's binding affinity, potency, or pharmacokinetics (Scheme 1C). To address this challenge, we turned our attention to organo-aluminum reagents. Despite being inexpensive, low in toxicity, and the most abundant metal in the Earth's crust, aluminum has been largely overlooked as a carbon radical precursor. This raises a fundamental question: can organoaluminum compounds generate alkyl radicals under photoredox conditions and participate in synthetically useful cross-coupling transformations (Scheme 1A ii)? While trimethyl-aluminum (AlMe₃) is a widely available commodity chemical and organo-aluminum compounds play a crucial role in largescale industrial processes such as the Ziegler-Natta polymerization, their application in laboratory settings has been limited by their pyrophoric nature and instability. Nevertheless, their lower nucleophilicity combined with pronounced Lewis acidity has enabled the development of a diverse cross- coupling chemistry (Scheme 1B). These polar strategies include the zirconium-catalyzed asymmetric carboalumination of alkenes (ZACA), a key method in total synthesis (Scheme 1B i), as well as nickel catalyzed cross-coupling reactions involving unactivated aryl electrophiles with aryl aluminum (Scheme 1B ii) or alkyl reagents (Scheme 1B iii). In designing our approach to address this challenge, we sought to avoid impractical aluminum reagents.