On the other end of the spectrum, electrochemistry has embraced the challenge of C(sp 3 ) radical cross-coupling for decades. The Kolbe reaction reported more than 170 years ago, represents one of the first examples of electrochemically driven decarboxylative C(sp 3 )-C(sp 3 ) crosscouplings. However, this reaction was neglected by the synthetic community owing to the highly oxidizing conditions and poor functional group tolerance. This report served as an inspiration for the Baran group in collaboration with our labs to develop a modern electrochemical solution to the challenge of C(sp 3 )-C(sp 3 ) cross-coupling. Rather than relying on the harsh oxidation of carboxylic acids, we chose to explore a comparatively easier reduction strategy by engaging the corresponding RAEs as coupling partners (Figure ). Now referred to as doubly decarboxylative cross-coupling (dDCC), the process is initiated by the cathodic reduction of a Ni(II) precatalyst to Ni(I). The generated Ni(I) can then activate the RAE through a reductive fragmentation process to produce an alkyl radical and a Ni(II) species. At this point, the Ni(II) species can either be reduced to provide a Ni(I) that is required to produce more alkyl radicals or accept an alkyl radical to form a Ni(III) species. These species can be further reduced and then trap another alkyl radical to form a Ni(III)R1R2(X) intermediate, which upon reductive elimination can forge the desired cross-coupled product and a Ni(I) species. An observable limitation of this coupling design is the lack of kinetic bias in the reduction of two different RAEs leading to a statistical distribution of cross-coupled and homo-coupled products. To overcome this synthetic limitation and minimize the production of the less desirablehomo-coupled products, a larger excess of one of the partners was required (1.5-3.0 equivalents). Another scope limitation in the initial report was the intolerance of α-heteroatom RAEs. When RAE substrates were used, cathodic reduction of the starting materials was observed with minimal formation of the desired cross-coupled product. As a mitigation strategy, the key silver nitrate additive from our previously developed C(sp 2 )-C(sp 3 ) decarboxylative arylation (vide supra) was leveraged and the in situ AgNP layer that forms on the cathode protects the reductively-labile RAE from cathodic reduction.