Regioselective Direct C-H Bond Heteroarylation of Thiazoles Enabled by an Iminopyridine-Based -Diimine Nickel(II) Complex Evaluated by DFT Studies

DirectC-H bond arylation is a highly effective method forsynthesizing arylated heteroaromatics. This method reduces the numberof synthetic steps and minimizes the formation of impurities. We reportan air- and moisture-stable iminopyridine-based & alpha;-diimine nickel(II)complex for direct C5-H bond arylation of thiazole derivatives.Under a low catalyst loading and performing the reactions at lowertemperatures (80 & DEG;C) under aerobic conditions, we produced mono-and diarylated thiazole units. Competition experiments and densityfunctional theory calculations revealed that the mechanism of C-Hactivation in 4-methylthiazole involves an electrophilic aromaticsubstitution.