Electrochemical Generation of a Nonstabilized Azomethine Ylide: Access to Substituted N-Heterocycles

Abstract

Azomethine ylides are fascinating 1,3-dipoles for [3 + 2] cycloaddition reactions toward the construction of N-heterocycles. Herein, an efficient and environmentally benign electrochemical approach for the generation of 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. This electrosynthetic methodology indulges a straightforward and facile approach for the construction of substituted pyrrolidines.

Palladium‐catalyzed sequential Heck/Suzuki coupling reaction and the synthesis of diarylmethanes in aqueous media using indole‐based N‐heterocyclic carbene precursors

“…1 H NMR (400 MHz, CDCl 3 ): δ 8.04 (d, J = 16.0 Hz, 1H), 7.63–7.59 (m, 2H), 7.33 (t, J = 8.0 Hz, 1H), 7.23 (t, J = 8.0 Hz, 1H), 6.39 (d, J = 16.0 Hz, 1H), 3.83 (s, 3H); 13 C NMR (101 MHz, CDCl 3 ): δ 166.8, 143.2, 134.5, 133.4, 131.2, 127.8, 127.7, 125.3, 120.7, 51.9. Spectroscopic data consistent with literature [60].…”

Electrochemical 1,3‐Oxofluorination of Gem‐Difluoro Cyclopropanes: Approach to α‐CF3‐Substituted Carbonyl Compounds

“…In the last decade, electro‐organic synthesis has emerged as a useful method for performing advantageous organic transformations [17] to achieve specific oxidative or reductive reactions such as decarboxylation, [18a] alkene bifunctionalization, [18b] rearrangements, [18c] annulations, [18d] and C−C or C‐heteroatom bond formation [18e–i] . In 2021, Lei et al .…”

Iodide-umpolung catalytic system for non-traditional amide coupling from nitroalkanes and amines

“…Starting materials 1a–d were prepared according to literature procedures. 31,32 1e–j and 1o were prepared based on a reported reaction protocol. 33 1k, 1l , 1n and 1t were prepared based on literature procedures.…”