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, Physical Chemistry

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, Physical Chemistry

Journal of Organic Chemistry

0022-3263 (ISSN) 1520-6904 (eISSN)

Vol. 85 21 13453-16465

Subject Categories

Inorganic Chemistry

Biocatalysis and Enzyme Technology

Organic Chemistry

DOI

10.1021/acs.joc.0c01412

More information

Latest update

1/5/2021 8