Open AccessAzulene Functionalization by Iron-Mediated Addition to a Cyclohexadiene Scaffold
Author(s) -
Petter Dunås,
Lloyd C. Murfin,
Oscar Nilsson,
Nicolas Jame,
Simon E. Lewis,
Nina Kann
Publication year - 2020
Publication title -
the journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.0c01412
Subject(s) - chemistry , azulene , surface modification , electrophile , ketone , derivatization , cationic polymerization , diene , yield (engineering) , combinatorial chemistry , conjugated system , photochemistry , coupling reaction , organic chemistry , catalysis , high performance liquid chromatography , materials science , polymer , metallurgy , natural rubber
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.
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