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Synthesis of dendritic oligo(aryl sulfone)s as supports for synthesis
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UNSPECIFIED (2005) Synthesis of dendritic oligo(aryl sulfone)s as supports for synthesis. TETRAHEDRON, 61 (52). pp. 12314-12322. doi:10.1016/j.tet.2005.09.103 ISSN 0040-4020.
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Official URL: http://dx.doi.org/10.1016/j.tet.2005.09.103
Abstract
A short, divergent route to G(1) oligo(aryl sulfone)s and a G(2) oligo(aryl sulfone) dendrimer using nucleophilic aromatic substitution reactions is described. A range of tetrasubstituted pentasulfones are proposed for applications as homogeneous supports for synthesis. Key to achieving selectivity in the syntheses is the activation of leaving groups by sulfide to sulfone oxidation. Preparation of the G(2) oligo(aryl sulfone) is low-yielding due to competition from SET processes that are interesting from a mechanistic point of view. The utility of the supports is exemplified with a four step synthesis of a dipeptide and by 'react and release' synthesis of amides. (c) 2005 Elsevier Ltd. All rights reserved.
Item Type: | Journal Article | ||||
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Subjects: | Q Science > QD Chemistry | ||||
Journal or Publication Title: | TETRAHEDRON | ||||
Publisher: | PERGAMON-ELSEVIER SCIENCE LTD | ||||
ISSN: | 0040-4020 | ||||
Official Date: | 26 December 2005 | ||||
Dates: |
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Volume: | 61 | ||||
Number: | 52 | ||||
Number of Pages: | 9 | ||||
Page Range: | pp. 12314-12322 | ||||
DOI: | 10.1016/j.tet.2005.09.103 | ||||
Publication Status: | Published |
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