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Azulene Functionalization by Iron-Mediated Addition to a Cyclohexadiene Scaffold

[Image: see text] The functionalization of azulenes via reaction with cationic η(5)-iron carbonyl diene complexes under mild reaction conditions is demonstrated. A range of azulenes, including derivatives of naturally occurring guaiazulene, were investigated in reactions with three electrophilic iro...

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Detalles Bibliográficos
Autores principales: Dunås, Petter, Murfin, Lloyd C., Nilsson, Oscar J., Jame, Nicolas, Lewis, Simon E., Kann, Nina
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7660747/
https://www.ncbi.nlm.nih.gov/pubmed/33085490
http://dx.doi.org/10.1021/acs.joc.0c01412
Descripción
Sumario:[Image: see text] The functionalization of azulenes via reaction with cationic η(5)-iron carbonyl diene complexes under mild reaction conditions is demonstrated. A range of azulenes, including derivatives of naturally occurring guaiazulene, were investigated in reactions with three electrophilic iron complexes of varying electronic properties, affording the desired coupling products in 43–98% yield. The products were examined with UV–vis/fluorescence spectroscopy and showed interesting halochromic properties. Decomplexation and further derivatization of the products provide access to several different classes of 1-substituted azulenes, including a conjugated ketone and a fused tetracycle.