Synthesis of nitrogen-containing 15-membered triacetylenic macrocycles. Stable complex with palladium(0)

Anna Pla-Quintana, Anna Roglans, Anna Torrent, Marcial Moreno-Mañas, Jordi Benet-Buchholz

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37 Citations (Scopus)

Abstract

Selective and efficient preparation of a new type of nitrogen-containing 15-membered triacetylenic macrocycles named 1,6,11-tris(arylsulfonyl)-1,6,11- triazacyclopentadeca-3,8,-13-triynes (1) (Ar1 = Ar2 = Ar3 = 4-methylphenyl, 1aaa; Ar1 = Ar2 = 4-methylphenyl, Ar3 = ferrocenyl, 1aab) has been achieved. Macrocycle 1aaa forms a very stable complex with Pd0, being the first palladium(O) complex with a macrocyclic triyne. The three triple bonds in 1aaa are responsible for the complexation. The X-ray structures of both the ligand 1aaa and its Pd0 complex are presented. Furthermore, compound 1aaa undergoes cycloisomerization into the corresponding 2,5,8-tris[(4-methlphenyl) sulfonyl]-2,5,8-triazatrindane, 11aaa, when treated with Pd(PPh 3)4 in refluxing toluene.
Original languageEnglish
Pages (from-to)2762-2767
JournalOrganometallics
Volume23
Issue number11
DOIs
Publication statusPublished - 24 May 2004

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