Multiring interlocked systems via transition metal-templated strategy: The single-cyclization synthesis of [3]-catenates

The synthesis of a potential precursor of a multi-interlocking ring system is described. This precursor consists of two lipophilic 4,7-di-(n-hexyl)-2,9-di-phenyl-1,10-phenanthroline moieties linked by a diacetylenic bridge and ended by two alkyne groups. The Cu(I)-templated double threading of this bis-chelate string into two coordinating macrocycles was demonstrated. An intramolecular cyclization (Glaser oxidation) of this preorganized system leads to the corresponding dicopper(I) [3]-catenate in 48% yield. Copyright (C) 1996 Elsevier Science Ltd