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Azulene functionalization by iron-mediated addition to a cyclohexadiene scaffold

Journal of Organic Chemistry, 2020-11, Vol.85 (21), p.13453-13465 [Peer Reviewed Journal]

ISSN: 0022-3263 ;ISSN: 1520-6904 ;EISSN: 1520-6904 ;DOI: 10.1021/acs.joc.0c01412

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  • Title:
    Azulene functionalization by iron-mediated addition to a cyclohexadiene scaffold
  • Author: Dunås, Petter ; Murfin, Lloyd C. ; Nilsson, Oscar J. ; Jame, Nicolas ; Kann, Nina
  • Subjects: Organic Chemistry
  • Is Part Of: Journal of Organic Chemistry, 2020-11, Vol.85 (21), p.13453-13465
  • Description: 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.
  • Language: English
  • Identifier: ISSN: 0022-3263
    ISSN: 1520-6904
    EISSN: 1520-6904
    DOI: 10.1021/acs.joc.0c01412
  • Source: Opus: University of Bath's Eprints IR
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