American Chemical Society
ol1c01735_si_001.pdf (12.86 MB)

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

Download (12.86 MB)
journal contribution
posted on 2021-07-02, 15:18 authored by Rikuo Kajiwara, Shibo Xu, Koji Hirano, Masahiro Miura
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.