Azulene functionalization by iron-mediated addition to a cyclohexadiene scaffold

Petter Dunås, Lloyd C. Murfin, Oscar J. Nilsson, Nicolas Jame, Simon E. Lewis, Nina Kann

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Abstract

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 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.

Original languageEnglish
Pages (from-to)13453-13465
Number of pages13
JournalJournal of Organic Chemistry
Volume85
Issue number21
Early online date21 Oct 2020
DOIs
Publication statusPublished - 6 Nov 2020

ASJC Scopus subject areas

  • Organic Chemistry

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