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Azulene Functionalization by Iron-Mediated Addition to a Cyclohexadiene Scaffold.

ABSTRACT: The functionalization of azulenes via reaction with cationic ?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.

SUBMITTER: Dunas P

PROVIDER: S-EPMC7660747 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature

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Azulene Functionalization by Iron-Mediated Addition to a Cyclohexadiene Scaffold.

Dunås Petter P Murfin Lloyd C LC Nilsson Oscar J OJ Jame Nicolas N Lewis Simon E SE Kann Nina N

The Journal of organic chemistry 20201021 21

The functionalization of azulenes via reaction with cationic η5-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 proper ...[more]

PMID: 33085490

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