Copper-Catalyzed Three-Component Redox-Neutral Ring Opening of Benzothiazoles to 1‑Amino‑N‑(2-(phenylthio)phenyl)methanimine

Copper-catalyzed three-component redox-neutral ring opening of benzothiazoles with aryl iodides and O-benzoyl hydroxylamines for the synthesis of 1-amino-N-(2-(phenylthio)­phenyl)­methanimine has been developed. This one-pot reaction undergoes C–S and N–O bond cleavage and new C–S and C–N bond construction. Several control experiments excluded a free radical procedure and also demonstrated the secondary amine as a possible intermediate, which was vital to the catalytic reaction. Meanwhile, the deuteration experiment got rid of the C–H activation dehydroisomerization of the benzothiazole mechanism.本研究开发了一种铜催化苯并噻唑（benzothiazoles）与芳基碘化物、O-苯甲酰基羟胺的三组分无氧化还原开环反应，用于合成1-氨基-N-(2-(苯硫基)苯基)甲亚胺。该一锅法反应涉及C-S键与N-O键的断裂以及新C-S键和C-N键的构建。多项对照实验排除了自由基反应路径，并证实仲胺可作为该催化反应的关键中间体。同时，氘代实验排除了苯并噻唑发生C-H活化脱氢异构化的反应机理。