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Synthesis 2002(13): 1898-1902
DOI: 10.1055/s-2002-33925
PAPER
© Georg Thieme Verlag Stuttgart · New York

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

Volker Böhmer*a, Vasiliy Bruskoa, Kari Rissanenb
a Fachbereich Chemie und Pharmazie, Abteilung Lehramt Chemie, Johannes Gutenberg-Universität, Duesbergweg 10-14, 55099 Mainz, Germany
Fax: +49(6131)3925419; e-Mail: vboehmer@mail.uni-mainz.de;
b Department of Chemistry, University of Jyväskylä, P.O. Box 35, 40351 Jyväskylä, Finland
Fax: +358(14)2602501; e-Mail: Kari.Rissanen@jyu.fi;
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Publikationsverlauf

Received 29 April 2002
Publikationsdatum:
09. September 2002 (online)

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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

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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.