Copper/iron-catalyzed Ullmann coupling of diiodo- and dibromoarenes and diphenols for the synthesis of aryl ether macrocycles

Diiodoarenes (or dibromoarenes) reacted with diphenols, catalyzed by Cul/Fe(acac)(3) in the presence of K2CO3 in anhydrous DMSO at 110 degrees C for 7 days under nitrogen atmosphere, to afford macrocyclic aryl ethers effectively. To expand this methodology, a cyclic hepta(p-phenylene oxide) and cyclic deca(pphenylene oxide) were synthesized in one pot. Some macrocyclic aryl ethers showed strong fluorescence in acetone at 25 degrees C. (C) 2014 Elsevier Ltd. All rights reserved.