Work

Aziridine Group Transfer via Transient N-Aziridinyl Radicals

Year: 2024

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide Aziridines are the smallest nitrogen-containing heterocycles. Strain-enhanced electrophilicity renders aziridines useful synthetic intermediates and gives rise to biological activity. Classical aziridine syntheses─based on either [2 + 1] cycloadditions or intramolecular substitution chemistry─assemble aziridines from acyclic precursors. Here, we introduce N- aziridinyl radicals as a reactive intermediate that enables the transfer of intact aziridine fragments in organic synthesis. Transient N- aziridinyl radicals are generated by the reductive activation of N -pyridinium aziridines and are directly characterized by spin-trapped EPR spectroscopy. In the presence of O 2, N -aziridinyl radicals are added to styrenyl olefins to afford 1,2-hydroxyaziridination products. These results establish aziridinyl radicals as new reactive intermediates in synthetic chemistry and demonstrate aziridine group transfer as a viable synthetic disconnection.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.4c14169

Authors: Promita Biswas, Asim Maity, Matthew T. Figgins, David C. Powers

Institution: Texas A&M University

Language: English

Topic: Synthesis and Catalytic Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Welch Foundation, National Institutes of Health, National Institute of General Medical Sciences