To further investigate the potential applicability of our reaction conditions to C(sp 2 )-C(sp 3 ) bond formation in molecules relevant to drug discovery, we performed a parallel library synthesis via late-stage diversification of aryl halide 5f, a precursor to oxazolidinone antibacterials, with different alkyl halides (Figure ). First, we optimized the loadings of bpy Ni and Co Pc for the reactions of 5f with a benzylic chloride, an alkyl iodide, and an alkyl bromide (see SI). We then used the optimized conditions for each class of alkyl halide to evaluate the coupling of a series of functionalized derivatives with 5f using HTE techniques (see SI). For example, all primary alkyl bromides used in the experiment were coupled under the optimal conditions determined for the coupling of 5f with 1-bromo-3-phenylpropane (6r). Using our strategy, we observed that 25 out of 32 products were formed in greater than 10% conversion, an overall 78% success rate. A range of functionalized primary benzyl chloride electrophiles could be coupled, including substrates containing a tetrazole (6b) or thiophene (6d) ring, or a protic amide substituent (6f). Further, various primary alkyl iodide and bromide electrophiles could be coupled, such as substrates containing an unprotected indole (6o) and terminal alkenes (6x), which are susceptible to Giese- type additions in related reactions. Additionally, heterocyclic rings, which are prevalent in medicinal chemistry, such as azetidine (6k), piperidine (6n), and cyclic ethers (6j, 6u, 6aa) are compatible with our method. Overall, this experiment shows that our methodology can tolerate a large number of functional groups on the alkyl halide substrate. It also shows that the optimized reactions conditions obtained for an individual aryl halide substrate can be readily translated to a broad range of alkyl halides without reoptimization, which enables efficient parallel library synthesis and should be valuable in medicinal chemistry.