Electrochemical generation of a nonstabilized azomethine ylide: access to substituted N-heterocycles Rakesh Kumar, Prabal Banerjee Indian Institute of Technology Ropar, India Azomethine ylides are nitrogen-containing 1,3-dipoles with an iminium ion adjacent to carbanion and are fascinating 1,3-dipoles for [3 + 2] cycloaddition reactions toward the construction of N -heterocycles. An efficient and environmentally benign electrochemical approach for generating a nonstabilized azomethine ylide has been established under metal-free and external oxidant-free conditions. The resulting 1,3-dipole undergoes a [3 + 2] cycloaddition reaction with olefins and a carbonyl group. This electrosynthetic methodology indulges a straightforward and facile approach for constructing substituted pyrrolidines andoxazolidines. References 1. Coldham, I.; Hufton, R. Intramolecular Dipolar Cycloaddition Reactions of Azomethine Ylides. Chem. Rev. 2005, 105, 2765- 2810. 2. Padwa, A.; Pearson, W. H.; Harwood, L. M.; Vickers, R. J. Azomethine Ylides. Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products. Chemistry of Heterocyclic Compounds: A Series of Monographs 2003, 59, 169-252. 3. Morin, M. S. T.; St-Cyr, D. J.; Arndtsen, B. A. HornerWadsworth-Emmons Reagents as Azomethin Ylide Analogues: Pyrrole Synthesis via [3 + 2] Cycloaddition. Org. Lett. 2010, 12, 4916-4919
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