Metal-Free Aziridination of Unactivated Olefins via Transient <i>N</i>-Pyridinium Iminoiodinanes.

ABSTRACT: We describe a metal-free aziridination of unactivated olefins to generate N-pyridinium aziridines. Subsequent cross-coupling affords N-aryl aziridines, and reductive depyridylation affords N-H aziridines. Kinetics experiments, based on a variable time normalization analysis (VTNA), indicate that aziridination proceeds via a highly electrophilic N-pyridinium iminoiodinane intermediate. These studies expand build-and-couple aziridine synthesis to unactivated olefins and introduce charge-enhanced electrophilicity into the chemistry of iminoiodinanes.

SUBMITTER: Tan H 

PROVIDER: S-EPMC11600189 | biostudies-literature | 2024 Nov

REPOSITORIES: biostudies-literature