Visible-Light-Induced [5 + 1] Annulation of Vinyl Cyclopropane with Nitrene

A metal- and reagent-free visible-light-mediated [5 + 1] annulation of vinyl cyclopropanes with iminoiodinanes has been developed, providing efficient access to 1,2,3,6-tetrahydropyridines with broad substrate tolerance for aryl, alkyl, and heteroaryl substituents. These scaffolds undergo base-promoted aromatization to 2,5-diarylpyridines and diverse transformations, highlighting their utility in medicinal and materials chemistry. Mechanistic studies reveal a triplet nitrene-initiated radical pathway involving selective cyclopropane ring opening, advancing sustainable C-N bond formation.

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Publication Details

Journal
Organic Letters
Published
2025-12-04
DOI
https://doi.org/10.1021/acs.orglett.5c04205
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
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article

Visible-Light-Induced [5 + 1] Annulation of Vinyl Cyclopropane with Nitrene

Janakiram Vaitla, Shalu Deshwal
Organic Letters
Radical Photochemical Reactions
article

Visible-Light-Induced [5 + 1] Annulation of Vinyl Cyclopropane with Nitrene

Janakiram Vaitla, Shalu Deshwal
article en

Abstract

A metal- and reagent-free visible-light-mediated [5 + 1] annulation of vinyl cyclopropanes with iminoiodinanes has been developed, providing efficient access to 1,2,3,6-tetrahydropyridines with broad substrate tolerance for aryl, alkyl, and heteroaryl substituents. These scaffolds undergo base-promoted aromatization to 2,5-diarylpyridines and diverse transformations, highlighting their utility in medicinal and materials chemistry. Mechanistic studies reveal a triplet nitrene-initiated radical pathway involving selective cyclopropane ring opening, advancing sustainable C-N bond formation.

Organic LettersVol. 27(50)
Indian Institute of Technology Delhi (IN)
Openalex Percentile: Top 71%
Radical Photochemical Reactions
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Visible-Light-Induced [5 + 1] Annulation of Vinyl Cyclopropane with Nitrene — Janakiram Vaitla, Shalu Deshwal · Organic Letters (2025) | TGRS Research Map | TGRS