Metal-Free Electrochemical [3+2] Cycloaddition between α-Amino Carbonyls and Tosylmethyl Isocyanide en route to Substituted Imidazoles

The established strategy unveils a metal and mediator-free electrochemical [3+2] cycloaddition approach among alpha-amino carbonyls and tosylmethyl isocyanide (TosMIC) fabricating substituted imidazole scaffolds. Implementation of electro-redox conditions on this cycloaddition approach eliminates the essential requirement of transition metal catalysts and chemical oxidants. A wide variety of different functionalities are well tolerated under this reaction condition, contributing to the substrate scope and applicability. Several control experiments and cyclic voltammetry studies suggest an electro-oxidation triggered successive C-C and C-N bond formations followed by rapid aromatization for constructing the five-membered core structure.

Automated summary

This study presents a metal and mediator-free electrochemical method for fabricating substituted imidazole scaffolds. The method involves electro-oxidation triggered successive bond formations and rapid aromatization, allowing the tolerance of various functionalities.