5-membered heterocycles represent an important challenge in the context of radical cross-coupling methodology. Such molecules are often underrepresented in the current C(sp 2 )-C(sp 3 ) radical cross-coupling literature. Given the functional group compatibility demonstrated above, several 5-membered heterocycles were targeted. Imidazole containing propellane 23 was generated from the corresponding iodoand bromo-imidazole coupling partners in 32% yield and 16% yield respectively. SEM-protected iodo-pyrazole was coupled with a secondary acyclic homoallylic redox active ester giving 24 in 20% yield. It is important to note that all the existing methods tested for DCC transformations failed to give more than trace yield of product for these challenging cross coupling partners. Thiazoles were able to perform well in this cross-coupling platform. Beta-glycine derivative 25 was generated from the corresponding bromo-and iodo-methylthiazole. Activation of the thiazole with an electron withdrawing bromine atom significantly improved the results of the cross coupling as evidenced by 26 which formed in 49% from the corresponding bromide. Notably, excellent chemoselectivity was observed between the second bromine atom on the thiazole as well as the pendant alkyl chloride on the redox active ester fragment. Finally, the RAE derived from unprotected chenodeoxycholic acid was coupled efficiently with 3iodothiophene to provide 27 in 58% yield. Such arylated cholic acid derivatives are usually synthesized through Minisci transformations limited to 6-membered heterocycles. Table . Contextualized Scope of the Ag-Ni Electrocatalytic DCC. Yields of isolated products are indicated in each case unless otherwise specified. a Yield determined by 1 H-NMR with 1,3,5-trimethoxybenzene as an internal standard.