Photochemical C3-amination of pyridines via Zincke imine intermediates
Kitti Franciska Szabó,
Piotr Banachowicz,
Antoni Powała,
Danijela Lunic,
Ignacio Funes Ardoiz () and
Dorota Gryko ()
Additional contact information
Kitti Franciska Szabó: Institute of Organic Chemistry Polish Academy of Sciences
Piotr Banachowicz: Institute of Organic Chemistry Polish Academy of Sciences
Antoni Powała: Institute of Organic Chemistry Polish Academy of Sciences
Danijela Lunic: Universidad de La Rioja
Ignacio Funes Ardoiz: Universidad de La Rioja
Dorota Gryko: Institute of Organic Chemistry Polish Academy of Sciences
Nature Communications, 2025, vol. 16, issue 1, 1-9
Abstract:
Abstract Selective skeletal and peripheral editing of the pyridine moiety has broadly expanded the chemical space. While C-H functionalization at C2 and C4 positions are enabled by the inherent reactivity of this heteroarene, selective derivatization at the C3 position has long posed a significant challenge. Recently, based on a dearomatization-rearomatization sequence, involving Zincke imine intermediates, selective halogenation (-Br, -Cl, and -I) and isotopic labelling were accomplished. Here, we report a mild and regioselective method for C3-amination that relies on the photochemical reaction of Zincke imine with an amidyl radical generated from N-aminopyridinium salts. Mechanistic and theoretical studies indicate that radical intermediates are involved and explain the C3 regioselectivity of the reaction.
Date: 2025
References: Add references at CitEc
Citations:
Downloads: (external link)
https://www.nature.com/articles/s41467-025-59809-9 Abstract (text/html)
Related works:
This item may be available elsewhere in EconPapers: Search for items with the same title.
Export reference: BibTeX
RIS (EndNote, ProCite, RefMan)
HTML/Text
Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-025-59809-9
Ordering information: This journal article can be ordered from
https://www.nature.com/ncomms/
DOI: 10.1038/s41467-025-59809-9
Access Statistics for this article
Nature Communications is currently edited by Nathalie Le Bot, Enda Bergin and Fiona Gillespie
More articles in Nature Communications from Nature
Bibliographic data for series maintained by Sonal Shukla () and Springer Nature Abstracting and Indexing ().