Arynes Promoted Dehydrosulfurization of Thioamides: Access to Nitriles and Diaryl Sulfides.

An aryne-promoted dehydrosulfurization reaction of thioamides to give nitriles and diaryl sulfides in a one-pot manner is presented. Aromatic, heteroaromatic, and aliphatic natural products and drug-derived nitriles and diaryl sulfides were obtained in good to excellent yields. Especially, selenoamide was also a suitable substrate and produced diaryl selenide and nitrile in high yields. The D-labeled experiments indicated that the protons of thioamides transfer to diaryl sulfides.