Synthetic Chameleon Turns into Oximes, Nitrones, and Hydroxylamines when Exposed to Blue Light

0584864 - ÚACH 2025 RIV US eng J - Journal Article
Marčeková, M. - Caletková, O. - Kalníková, R. - Litecká, Miroslava - Moncol’, J. - Jakubec, P.
Synthetic Chameleon Turns into Oximes, Nitrones, and Hydroxylamines when Exposed to Blue Light.
ACS Omega. Roč. 9, č. 12 (2024), s. 14262-14268. ISSN 2470-1343. E-ISSN 2470-1343
Institutional support: RVO:61388980
Keywords : Functional groups,,,, * Nitrogen compounds * Organic synthesis * Photochemical reactions * Redox reactions
OECD category: Inorganic and nuclear chemistry
Impact factor: 4.1, year: 2022
Method of publishing: Open access

A metal-free, user-friendly photochemical transformation of nitroalkanes to oximes, nitrones, and hydroxylamines has been developed. The visible-light-induced reactions are catalyzed by the readily available photoredox organocatalyst 4CzIPN and use inexpensive amines as reductants. Broad in scope and tolerant of multiple functional groups and heterocycles, the transformation proceeds under mild conditions. Its synthetic potential was demonstrated in the formal total synthesis of amathaspiramide F. A basic insight into the reaction mechanism was gained with the help of an NMR study.
Permanent Link: https://hdl.handle.net/11104/0352651


Research data: ACS Publications