Macrobicycles comprising a central diazacrown structural unit were modified with two
3-bromobenzyl substituents and the resulting compounds were introduced in Pd(0)-catalyzed macrocyclization
reactions with trioxadiamine, to give cryptand-like macrotricycles. In the second approach,
diazacrown ethers were substituted with two 3,5-dibromobenzyl groups and their Pd(0)-catalyzed double
macrocyclization with a series of oxadiamines produced a new family of trimacrocyclic compounds;
the Pd(dba)2/RuPhos catalytic system was found to be the most efficient. The decoration of
one trimacrocycle with four dansyl fluorophore groups produced a fluorescent molecular probe for
Cu(II) and Al(III) cations.
Keywords: Amination, cryptands, diazacrown ethers, macrocycles, Pd catalysis, polyamines.
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