Bipyridine-Type Bidentate Auxiliary-Enabled Copper-Mediated C–H/C–H Biaryl Coupling of Phenols and 1,3-Azoles

A copper-mediated dehydrogenative C–H/C–H biaryl coupling of phenols and 1,3-azoles has been developed. The key to its success is the introduction of a bipyridine-type bidentate auxiliary, 4,4′-di­(tert-butyl)-2,2′-bipyridine, on the phenol oxygen, which is readily prepared and easily attachable, detachable, and recyclable. The reaction proceeds smoothly in the presence of copper salt alone to form the corresponding phenol-azole heterobiaryls, which are prevalent motifs in functional molecules such as excited-state intramolecular proton transfer materials.