Highly efficient copper/palladium-catalyzed tandem Ullman reaction/arylation of azoles via C-H activation: Synthesis of benzofuranyl and indolyl azoles from 2-(gem-dibromovinyl)phenols(anilines) with azoles

摘要

In this paper, a novel and highly efficient copper/palladium-catalyzed tandem intramolecular Ullman-type C-O(N) coupling reaction of 2-(gem-dibromovinyl)phenols(anilines) followed by an intermolecular arylation of azoles through C-H activation has been developed. In the presence of CuBr with Pd(PPh_3)_2Cl_2 used as co-catalyst, and LiO ~tBu as a base, the one-pot reactions of 2-(gem-dibromovinyl)phenols and 2-(gem-dibromovinyl)anilines with a variety of azoles, including oxazoles, imidazoles, thiazoles, and oxadiazoles underwent smoothly in toluene at 100 °C to generate the corresponding biheteroaryl products in high yields. A tentative mechanism of copper/palladium-catalyzed tandem reaction was described.