Rotaxanation as a sequestering template to preclude incidental metal insertion in complex oligochromophores

The high yielding Cu I -mediated click reaction is an effective procedure for the preparation of oligoporphyrinoid conjugates. However, the Cu I catalyst leads to the adventitious and usually undesirable insertion of Cu ions into any non-metalated porphyrinoid centers during reaction. Here we report...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2020-07, Vol.56 (54), p.7447-745
Hauptverfasser: Ngo, Huynh Thien, Lewis, James E. M, Payne, Daniel T, D'Souza, Francis, Hill, Jonathan P, Ariga, Katsuhiko, Yoshikawa, Genki, Goldup, Stephen M
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Sprache:eng
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Zusammenfassung:The high yielding Cu I -mediated click reaction is an effective procedure for the preparation of oligoporphyrinoid conjugates. However, the Cu I catalyst leads to the adventitious and usually undesirable insertion of Cu ions into any non-metalated porphyrinoid centers during reaction. Here we report a "sacrificial rotaxane" strategy for the multifunctionalization of porphyrins with free base corroles without incidental copper insertion. This strategy can be considered a general method for implementing Cu I -mediated click reactions with metal cation sequestration to avoid detrimental effects caused by the presence of copper cations. Rotaxane as sacrificial template to avoid metal insertion in porphyrinoids during copper catalyzed click reaction.
ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc09681g