Extended Calix[8]arenes by Sonogashira Cross-Coupling with Ethynylarenes

Abstract

Octabromo and -iodo derivatives of calix[8]arene were prepared in 85% and 73% yields and structurally confirmed by NMR, MS and IR spectroscopy and by the formation of ether or ester derivatives. The octaiodocalix[8]arene was successfully used in Sonogashira cross-coupling reactions for the preparation of p-arylethynylcalix[8]arenes. A single crystal X-ray structure of the starting calix[8]arene 1a shows the molecule in a centrosymmetric conformation, where four of the six pyridine solvent molecules are H-bonded to the hydroxyl groups.

Key words

calixarenes - halogenation - cross-coupling - palladium - catalysis

References

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22

The preparation follows Gutsche’s protocol [2] using a modification by Z. Asfari, private communication.

25

Crystallographic data for the structural analysis have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication, CCDC No 184339.