The analogy to two-dimensional heteroarene functionalization, the zeitgeist for over fifty years, is apt. In that world, electrophilic aromatic halogenation (EAH) followed by cross-coupling is a tried and true approach that has and continues to be employed on a daily basis. Proposed herein and demonstrated through this proof-of-concept study is a model wherein biocatalytic C-H oxidation and radical based cross couplings on three dimensional systems are akin to EAH and polar cross couplings (mostly Pd-based) in two dimensions. This study points to a uniquely powerful approach to both medicinal and process chemists that maximizes synthetic ideality and rapid SAR exploration and minimizes chiral resolution steps, expensive chiral ligands, and precious metal catalysts.