Photocatalytic [4 + 1] Annulation of Vinyl Aziridines with Alkyl Halides

Herein, we develop a photocatalytic [4 + 1] annulation of vinyl aziridines with alkyl halides. The reaction appears to experience radical trigger kinetically favored β-scission of the vinyl aziridine C-N bond, generating transient nitrogen-centered radical, followed by sequential single electron oxidation, 5-exo-trig cyclization, and protonation. Significantly, an unprecedented annulation mode in which vinyl aziridines serve as four-atom synthons has been disclosed.

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Publication Details

Journal
Organic Letters
Published
2026-03-23
DOI
https://doi.org/10.1021/acs.orglett.6c00743
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
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article

Photocatalytic [4 + 1] Annulation of Vinyl Aziridines with Alkyl Halides

Y. Liu, Jinghan Zhang, Jingjing Zhao, Dan Wang et al.
Organic Letters
Radical Photochemical Reactions
article

Photocatalytic [4 + 1] Annulation of Vinyl Aziridines with Alkyl Halides

Y. Liu, Jinghan Zhang, Jingjing Zhao, Dan Wang, Pan Li
article en

Abstract

Herein, we develop a photocatalytic [4 + 1] annulation of vinyl aziridines with alkyl halides. The reaction appears to experience radical trigger kinetically favored β-scission of the vinyl aziridine C-N bond, generating transient nitrogen-centered radical, followed by sequential single electron oxidation, 5-exo-trig cyclization, and protonation. Significantly, an unprecedented annulation mode in which vinyl aziridines serve as four-atom synthons has been disclosed.

Organic Letters
Henan University (CN)
Clean water and sanitation
Openalex Percentile: Top 11%
Radical Photochemical Reactions
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