Notably, bioactive molecules such as lauric acid and oleic acid, as well as the common herbicide 2,4-dichlorophenoxy acetic acid, were successfully employed as reaction partners with 3a, furnishing the corresponding functionalized products (53-55) in synthetically useful yields. We subsequently examined the scope of freshly prepared 1,1-diarylolefins and found that a diverse set of para-substituted symmetric examples were viable acceptors for the cyclohexyl radical. A trend became apparent between efficiency and electronics of the 1,1-diarylolefins. Strongly and moderately electron donating groups (methoxy and methyl, respectively) gave moderate and good product yields (56 and 57), while high product yields resulted from electron withdrawing substituent (F, Br, Cl) bearing SOMOphiles (58, 59 and 61). This is likely due to enhanced polarity matching in the Giese-type radical addition step involving the nucleophilic radical. 72,73 4,4'-(Ethene-1,1-diyl)bis(bromobenzene) could also be coupled with γ-tetrahydropyranyl radical, albeit in lower product yield (60). Asymmetric 1,1-diarylolefins were successfully functionalized with both primary and secondary radicals (62-64). Finally, substrates containing heteroaromatic rings were well-tolerated under the proposed conditions, enabling access to pyridine containing scaffolds not reported in the aforementioned photocatalytic methods (65 and 66). Notably, the thiophene-bearing structure 67 was isolated as a single diastereoisomer, whose (Z)-configuration was unambiguously confirmed by single-crystal XRD analysis.