Synthesis of N-Sulfonyl Amidines and 1,3,4-Oxadiazoles through Electrochemical Activation of DMF

Electrochemical routes for the synthesis of N-sulfonyl amidines and 1,3,4-oxadiazoles are reported through the activation of DMF molecule. Successful implementation of electro-redox on dehydrative coupling and oxidative cyclization reactions eliminates the necessity of stoichiometric chemical oxidants and minimizes the generation of reagent waste. Both protocols exhibited broad functional group tolerance, permitting a widespread substrate scope with 47-94% isolated yield. Several control experiments and cyclic voltammetry studies were performed and mechanistic details of these transformations are thoroughly outlined.

Automated summary

Electrochemical routes for the synthesis of N-sulfonyl amidines and 1,3,4-oxadiazoles are reported through the activation of DMF molecule. The successful implementation of electro-redox reactions eliminates the need for stoichiometric chemical oxidants and minimizes reagent waste generation. Both protocols exhibit broad functional group tolerance, allowing a wide substrate scope with 47-94% isolated yield. Several control experiments and cyclic voltammetry studies were conducted, providing detailed mechanistic insights into these transformations.