In addition to our work in photochemically driven C-O cross-coupling, a collaboration with the Baran group yielded a complimentary electrochemical approach (Figure ). The explicit mechanism of this electrochemical variant is still uncertain but is expected to follow a similar paired electrolysis mechanism as the electrochemical C-N coupling (vide supra). Control experiments suggest the need for paired electrolysis to carry out the reaction suggesting both oxidative and reductive events are critical to the overall bond-forming process. The preparative electrochemical C-O cross-coupling employs a cheap Ni(II) precatalyst and di-tert-butyl bipyridyl (dtbbpy) ligand framework and proceeds in a user-friendly undivided cell setup. The addition of molecular sieves to the reaction significantly improved the performance as trace water was found to be deleterious. The reaction tolerates a wide range of aryl bromide and alcohol coupling partners used in excess. Owing to the mild oxidative environment of the anode, tertiary alkyl amines are tolerated. Such functionality was shown to be a critical hindrance to the performance of photochemically driven couplings in head-to-head comparisons. Additionally, select substrates were scaled to decagram quantities and many applications to pharmaceutically relevant motifs were exemplified. While a powerful electrochemical approach to C-O coupling, limitations include the inability to couple tertiary alcohols and electron-rich azoles. Alternate bond disconnections could afford these challenging chemotypes leveraging electrogenerated cations also developed by the Baran group. However, such highly oxidizing methods and the weak nucleophilicity of phenoxides may hamper such efforts.