Metal-Free Aziridination of Unactivated Olefins via Transient <i>N</i> -Pyridinium Iminoiodinanes
Hao Tan, Phong Thai, Uddalak Sengupta, Isaac R. Deavenport, Cali M. Kucifer, David C. Powers
Abstract
High Resolution Image Download MS PowerPoint Slide 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.
Topics & Concepts
PyridiniumTransient (computer programming)MetalChemistryMedicinal chemistryOrganic chemistryComputer scienceProgramming languageSynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques