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Issue 2, 2016
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Arylation of thiacalix[4]arenes using organomercurial intermediates

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Abstract

Direct mercuration of thiacalix[4]arenes immobilized in the cone or 1,3-alternate conformations followed by Pd-catalyzed arylation was applied to achieve either meta- or para-substitution of basic skeletons. The arylated products represent unique substitution patterns in thiacalixarene chemistry and their conformational behaviour was studied using a combination of dynamic NMR techniques and X-ray crystallography. The usefulness of organomercurial intermediates was also demonstrated through the preparation of thiacalix[4]arene dimers so far unknown in thiacalixarene chemistry.

Graphical abstract: Arylation of thiacalix[4]arenes using organomercurial intermediates

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Article information


Submitted
10 Sep 2015
Accepted
03 Nov 2015
First published
10 Nov 2015

New J. Chem., 2016,40, 1104-1110
Article type
Paper

Arylation of thiacalix[4]arenes using organomercurial intermediates

F. Botha, V. Eigner, H. Dvořáková and P. Lhoták, New J. Chem., 2016, 40, 1104
DOI: 10.1039/C5NJ02427G

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