Regioselective Addition of Sulfur and Amine Nucleophiles To Assemble SC–S, S–N, and Umpolung C–N Bonds: Exploration of the −CBr3 Group as a Synthetic Equivalent of SC–S

The regioselective addition of sulfur and amine nucleophiles to a −CBr3 unit and nitromethyl moiety in a molecule with the installation of a five-diverse bond structure to novel isothiazole-5­(2H)-thione is demonstrated. Umpolung of the nitromethyl group leads to a novel scaffold with selective C–N bond formation. Consequently, differentiating reactive centers by sulfur and amine nucleophiles has been proposed to create unique S–N bonds in conjunction with the dithioate (SC–S−) moiety. This protocol allows for exploration of the −CBr3 moiety as a synthetic equivalent of the dithioate (SC–S−) unit during the reaction.