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Iron-Mediated Photochemical Anti-Markovnikov Hydroazidation of Unactivated Olefins

[Image: see text] Unactivated olefins are converted to alkyl azides with bench-stable NaN(3) in the presence of FeCl(3)·6H(2)O under blue-light irradiation. The products are obtained with anti-Markovnikov selectivity, and the reaction can be performed under mild ambient conditions in the presence of...

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Detalles Bibliográficos
Autores principales: Lindner, Henry, Amberg, Willi M., Carreira, Erick M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10591317/
https://www.ncbi.nlm.nih.gov/pubmed/37811819
http://dx.doi.org/10.1021/jacs.3c09122
Descripción
Sumario:[Image: see text] Unactivated olefins are converted to alkyl azides with bench-stable NaN(3) in the presence of FeCl(3)·6H(2)O under blue-light irradiation. The products are obtained with anti-Markovnikov selectivity, and the reaction can be performed under mild ambient conditions in the presence of air and moisture. The transformation displays broad functional group tolerance, which renders it suitable for functionalization of complex molecules. Mechanistic investigations are conducted to provide insight into the hydroazidation reaction and reveal the role of water from the iron hydrate as the H atom source.