Photoredox-Promoted Selective Synthesis of C-5 Thiolated 2-Aminothiazoles from Terminal Alkynes

A mild photoredox approach enabling the first one-step synthesis of thiolated 2-aminothiazoles has been reported. Notably, the incorporation of thio group on electron-rich heteroarenes such as aminothiazoles via conventional nucleophilic aromatic substitution (SNAr) presents a significant challenge owing to polarity mismatch. Herein, we present a remarkable site-selective installation of thio group at the C-5 position of the electron-rich aminothiazole skeleton and successfully used them for the postfunctionalization of drugs and natural products.

Automated summary

A mild photoredox approach for the one-step synthesis of thiolated 2-aminothiazoles has been reported. Incorporating a thio group onto electron-rich heteroarenes such as aminothiazoles using conventional nucleophilic aromatic substitution presents a significant challenge due to polarity mismatch. This study demonstrates a remarkable site-selective installation of a thio group at the C-5 position of the electron-rich aminothiazole skeleton, and its successful application for the postfunctionalization of drugs and natural products.