A new type of convergent paired electrochemical synthesis of sulfonamides under green and catalyst-free conditions

Abstract

Our main goal in this work is to synthesize valuable sulfonamide compounds according to the principles of green chemistry and also to present a unique convergent paired mechanism for their synthesis. In this study, we introduced a new type of convergent paired electro-organic synthesis of sulfonamide derivatives via a catalyst, oxidant, halogen and amine-free method. In this research, instead of using toxic amine compounds, an innovative mechanism based on the reduction of nitro compounds and in-situ production of amine compounds was used. The mechanism of electrophile generation is the cathodic reduction of the nitro compound to the hydroxylamine compound and then the anodic oxidation of the hydroxylamine to the nitroso compound. On the other hand, the nucleophile generation mechanism involves the two-electron oxidation of sulfonyl hydrazide to related sulfinic acid at the anode surface. The reaction leading to the synthesis of sulfonamides involves a one-pot reaction of the generated nitroso compound with the produced sulfinic compound.