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

Autor:	Tan H; Department of Chemistry, Texas A&M University, College Station, Texas 77843, United States., Thai P; Department of Chemistry, Texas A&M University, College Station, Texas 77843, United States., Sengupta U; Department of Chemistry, Texas A&M University, College Station, Texas 77843, United States., Deavenport IR; Department of Chemistry, Texas A&M University, College Station, Texas 77843, United States., Kucifer CM; Department of Chemistry, Texas A&M University, College Station, Texas 77843, United States., Powers DC; Department of Chemistry, Texas A&M University, College Station, Texas 77843, United States.
Jazyk:	angličtina
Zdroj:	JACS Au [JACS Au] 2024 Oct 10; Vol. 4 (11), pp. 4187-4193. Date of Electronic Publication: 2024 Oct 10 (Print Publication: 2024).
DOI:	10.1021/jacsau.4c00556
Abstrakt:	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. Competing Interests: The authors declare no competing financial interest. (© 2024 The Authors. Published by American Chemical Society.)
Databáze:	MEDLINE
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