First, a suitably functionalized gem-disubstituted precursor needed to be identified that was easy to make, stable to storage, and reliably engaged in stepwise cross-couplings. Secondly, a means to couple the resulting tertiary benzylic system to form the requisite gem-diarylated quaternary center needed to be uncovered. The formation of quaternary centers through direct cross-coupling has become a vibrant area of inquiry due to the inherent benefits of such an approach. Numerous studies have revealed the difficulty in arylating benzylic tertiary carbons, and to the best of our knowledge, there are no methods reported for the cross-coupling of benzylic tertiary cyclobutanoic systems (by radical or polar means). To address the first challenge, Table outlines selected coupling partner candidates that were evaluated. Gem-dibromo-cyclobutane 17 (Table ) is an obvious first candidate, but unfortunately selective activation of only one bromine atom proved problematic with only traces of arylated adducts observed (SM fully consumed). Next, malonic acid derivatives (18) were evaluated but the corresponding mono-RAE adducts were only formed in poor yield.