Silver-Catalyzed Dehydrogenative Cross-Coupling Of Heteroarenes

Heteroarometic biarys are the important structural motifs in advanced material, liquid crystal materials, ligands, pharmaceuticals and natural products. Although there are so many methods for linking two heteroaryls, coupling reaction is more high-efficiency. Traditional method for synthesis of biheteroaryls is via transition metal catalyzed cross-coupling which requires heteroaryl halide and heteroaryl organomatallic reagent as the preactivated substrate, it is disadvantageous in atom economy. In the past few years, the dehydrogenative coupling of heteroaryls attract great attention.In our study, we describe a dehydrogenative coupling reaction of two similar nature oxazole and thiazole, we also explore influence of CuⅡ for the reactivity. There are two parts in my paper:I. Optimizing the reaction conditions:screenning various of bases, catalysts, oxidant, solvent and reaction’s temperature and time.The optimum conditions:AgF (20 mmol%), Cu(OAc)2 (2-3 equiv), KF/CsF(3 equiv), in DMSO under Ar or O2 atmosphere, the highest yield is up to 99%. II. Proposing the possible mechanism:We propose the possible mechanism by analysing the results and the published literatures.