The invention of a direct electrochemical-promoted Glutarimide Cross-Coupling (GCC) using 1 was initially explored with bromopyridine 4 -(Table ). Although other radical precursors were considered and evaluated, 1 is the least expensive and most convenient. In its fully optimized form, GCC is extraordinarily simple and convenient to conduct open to the air in an undivided cell without regard to residual moisture and air: After mixing 1 (1.5 equiv, $9.00/g) and aryl halide 4 in NMP, NiCl2•6H2O (20 mol%, $0.02/g), bipy (20 mol%, $0.08/g), TBABF4 (1.0 equiv, $0.96/g), LiCl (2.5 equiv, $0.05/g), and AcOH (1.5 equiv, $0.26/l) are added. Subsequent electrolysis at room temperature for 5 hours results in a 78% isolated yield of 5 (entry 1). Not surprisingly, rudimentary control studies (entries 2-4) demonstrate the need for Ni, ligand, and electricity. One of the two main breakthroughs of this study, however, was the finding that a Brønsted-acid enabled this transformation as shown in entry 5. While numerous proton-sources can facilitate the reaction, AcOH was chosen due to its low cost, ease of removal, broad functional group tolerance and highest performance of acids screened (see SI). The use of acid additives is rare in Ni-based cross-couplings and, to our knowledge, without precedent for Ni-electrocatalysis. Indeed, this unusual inclusion is counterintuitive due the potential of undesired proto-dehalogenation and/or reduction reactions. As the resistance is low due to the acid additive, an electrolyte is not necessary but its inclusion increases overall conversion by 10-20% (entry 6). The addition of LiCl, however, is essential to achieve reasonable catalyst turnover and may serve a variety of roles (entry 7). It is interesting to note that the use of NiBr2 in place of NiCl2 (in the absence of LiCl) completely shuts down the reaction (entry 8). Increasing the catalyst loading to 40 mol% in the absence of LiCl results in only a single turnover of the catalyst (entry 9). The use of AgNO3, an additive that is quite beneficial in the coupling of redox-active esters, has no beneficial effect in this reaction (entry 10). Lowering the catalyst loading to 10 mol% only has a modest effect on the yield (entry 11) and a full 6 F/mol of electrons results in the highest conversion (entry 12).