Department of Chemistry and Chemical Engineering, Chalmers University of Technology, SE-41296 Gothenburg, Sweden.
Department of Chemistry, University of Bath, Convocation Avenue, Bath BA2 7AY, U.K.
J Org Chem. 2020 Nov 6;85(21):13453-13465. doi: 10.1021/acs.joc.0c01412. Epub 2020 Oct 21.
The functionalization of azulenes via reaction with cationic η-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.
通过与温和反应条件下的阳离子η-铁羰基二烯配合物反应，实现了蓝烯的功能化。研究了一系列蓝烯，包括天然存在的愈创蓝烯的衍生物，与三种具有不同电子性质的亲电铁配合物反应，以 43-98%的产率得到所需的偶联产物。用紫外可见/荧光光谱法对产物进行了检查，显示出有趣的变色性质。产物的脱配合和进一步衍生化提供了几种不同类别的 1-取代蓝烯，包括一个共轭酮和一个稠合的四环。
