Azulene functionalization by iron-mediated addition to a cyclohexadiene scaffold
Journal article, 2020
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.
Author
Petter Dunås
Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry
University of Bath
Lloyd C. Murfin
University of Bath
Oscar J. Nilsson
Student at Chalmers
Nicolas Jame
Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry
Simon E. Lewis
University of Bath
Nina Kann
Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry
Journal of Organic Chemistry
0022-3263 (ISSN) 1520-6904 (eISSN)
Vol. 85 21 13453-16465Subject Categories
Inorganic Chemistry
Biocatalysis and Enzyme Technology
Organic Chemistry
DOI
10.1021/acs.joc.0c01412