Established enantioselective methods to indole-containing heterobiaryl compounds include aryl-aryl coupling, desymmetrization of prochiral biaryls, and de-novo construction of the aryl rings. Despite the significant advances, generally applicable enantioselective synthesis is still challenging, primarily because of the conformational instability of the chiral axis connecting the five-membered ring, when compared to a six-membered ring (Scheme 1B). In fact, presently available atropselective syntheses of indoles with a chiral axis at C3 frequently necessitate bulky groups at C2, such as t-butyl or CHAr2. Use of N-hydroxyindoles as a umpoled indole equivalent may offer a redox-neutral C-H functionalization of indoles. , Building upon this premise, we recently demonstrated a successful C-H/C-H coupling of N-carboxyindoles with phenols in a highly chemo-and regioselective manner. In pursuit of advancing this process, leveraging an enantioselective transition metal-catalysis with a novel modality will be highly valuable, considering that early advance in atropselective indolyl biaryl cross-coupling has been made mostly with organocatalysis. . Copper-, iron-, and vanadium catalysts have been extensively studied in the oxidative coupling of 2-naphthols. Furthermore, Smith and coworkers recently reported Fe-catalyzed oxidative coupling of indolyl-naphthols. In these instances, presence of a coordinating group at C3 of 2-naphthols has proven necessary (Scheme 1B), presumably because bidentate chelation is crucial for enantiocontrol and the redox potential of 2naphthols may be attuned for chemoselective cross-coupling. Consequently, a novel heterobiaryl coupling that accommodates diverse phenolic partners, including 2-naphthols devoid of C3-substituents, would significantly broaden the functional diversity of the indolyl-phenol biaryl compounds.