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.
Authors
- Janakiram Vaitla (ORCID: https://orcid.org/0000-0003-4068-5916)
- Shalu Deshwal
Institutions
- Indian Institute of Technology Delhi (IN)
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
- 0.00