Functionalization of Primary C-H Bonds in Picolines toward Pyridylthioamides

We report a method for coupling of nitroarenes, 2- or 4-methylazaarenes, and elemental sulfur to afford (2-pyridyl)aryl thioamides. Good tolerance of functionalities was observed, including primary and secondary amines, bromo, iodo, ester, and boronic ester groups. Thioamides derived from pyrazole, thiazole, quinoline, quinoxalines, and azoles were obtained in good yields, showing the compatibility of heterocycles. This appears to be a general method to obtain pyridyl thioamides in one step from commercial, simple substrates.