Metal-Free Aziridination of Unactivated Olefins via Transient N-Pyridinium Iminoiodinanes

23 May 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

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

Keywords

aziridination
N-aminopyridinium salts
unactivated olefins
metal-free
C–N cross-coupling

Supplementary materials

Title
Description
Actions
Title
Supporting Information
Description
Experimental details and characterization data.
Actions

Comments

Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.