Synthesis of α-aminoketones from N-sulfonyl-1,2,3-triazoles via N-sulfinyl imines generated by intramolecular oxygen transfer

Abstract

A general procedure for intramolecular oxygen transfer from sulfonyl to a carbenoid carbon was established, extending the reaction mode of the corresponding common N-sulfonyl-1,2,3-triazoles. Indoles, and some other arenes, were employed as nucleophiles to react with the resulting key N-sulfinyl imine intermediate, and valuable α-aminoketones could be synthesized conveniently. The synthetic utility of the products was further exhibited by convenient synthesis of gem-diaryl ketones and densely substituted pyrrole. A tentative reaction mechanism was proposed according to control experiments.