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.

Abstract

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.