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Paper | Special issue | Vol 88, No. 2, 2014, pp.1213-1231
Published online, 14th August, 2013
DOI: 10.3987/COM-13-S(S)87
Synthesis of Macrobicycles Comprising 2,7-Diaminonaphthalene Moiety via Palladium-Catalyzed Amination Reaction

Alexei N. Uglov, Georgii A. Zubrienko, Anton S. Abel, Alexei D. Averin, Olga A. Maloshitskaya, Alla Bessmertnykh-Lemeune, Franck Denat, and Irina P. Beletskaya*

*Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1-3, 119991, Moscow, Russia


An original synthetic approach to bismacrocyclic ligands bearing naphthalene moiety was developed. First, the macrocycles comprising 2,7-diaminonaphthalene fragment were reacted with 2,7-dibromonaphthalene, 4,4’-dibromobiphenyl or bromobenzyl bromide affording corresponding N,N’-bis(bromoaryl) or N,N’-bis(bromobenzyl) substituted macrocycles. Pd-catalyzed macrocyclization of these compounds with a wide range of di- and polyamines led to a series of new macrobicyclic ligands. The yields of the macrobicycles are strongly dependent on the nature of starting compounds, reaching 35% in some cases.