We have described a process for the enantioselective synthesis of atropisomeric heterobiaryl derivatives via a direct oxidative cross-coupling that constructs the key biaryl linkage from two C-H bonds. This reaction utilizes a cheap and abundant Fe catalyst in the presence of a readily available chiral PyBOX ligand to enable a remarkably chemoselective cross-coupling between indoles and phenols. We envision that this process will enable the application of these and similar heterobiaryl compounds across the fields of materials science, catalysis and medicine.