Molecular scaffolds featuring strained four-membered rings have become increasingly popular in medicinal chemistry due to their ability to modulate the pharmacokinetic and pharmacodynamic profiles of drug candidates. These motifs can lead to increased solubility, greater metabolic stability, and improved interactions between receptors and ligands. Cyclobutanes, azetidines, and oxetanes in particular have been demonstrated to be useful isosteric replacements for aryl rings, piperidines, and carbonyl compounds, respectively. A careful study of the patent literature reveals that gem(1,1)-diaryl-substituted four membered rings, in particular, are highly coveted structures (Figure ) for which simple and modular synthetic pathways are nonexistent. Indeed, despite the apparent demand for such scaffolds, their synthesis remains largely confined to stepwise two-electron approaches, which face severe limitations (Figure ). For instance, classical methods for synthesizing (1,1)-diaryl cyclobutanes, such as Lewis acid-promoted Friedel-Crafts reactions (on 7) , present issues like ring opening and rearrangements. Alternative approaches, including transition metal-catalyzed arylation and Brønsted acidcatalyzed hydroarylation of cyclobutenes (8), are also limited, being strictly confined to the installation of electronrich arenes and suffering from reduced substrate scope and functional group compatibility. The most popular approach to access these molecules relies on antiquated carbonyl-based enolate chemistry that is inherently limited due to chemoselectivity concerns (strong bases, 10 or 11 to 12) and condensation chemistries used to convert the resulting carboxy/cyano functional group (12 to 13) into a heteroarene. To be sure, double enolate alkylations on systems like 10 are often low yielding and intolerant of numerous functional groups and although Pd-arylation of systems like 11 is precedented, its strict requirement for air-and moisture-free conditions (glovebox) complicates its practicality in a medicinal chemistry setting. Ultimately, construction of the second aryl group is restricted primarily to N-based heterocycles at the 2-position which drastically limits diversity space and often involves multistep sequences with each reaction demanding distinct conditions, making parallel screening of different ring systems inefficient. This study discloses a fundamentally different approach ideally suited to those engaged in drug discovery wherein 1,1-diaryl cyclobutanes, azetidines, and oxetanes are assembled through two sequential C-C couplings on abromoacids (14, Figure ). In this triply convergent approach, Ni-electrocatalysis enables modular, stepwise couplings first on the a-bromo substituent followed by decarboxylative cross coupling to access valuable gem-diaryl substitution in a programmable manner. The exceptional modularity, high tolerance towards various functional groups, and flexibility to incorporate both electron-poor and rich (hetero)arenes, opens a portal to easily access previously unexplored and elusive chemical space.