Harnessing the Dual Properties of Thiol-Grafted Cellulose Paper for Click Reactions: A Powerful Reducing Agent and Adsorbent for Cu

A new approach exploiting the dual properties of thiol‐grafted cellulose paper for promoting copper‐catalyzed [3+2]‐cycloadditions of organic azides with alkynes and adsorbing residual copper species in solution was developed. The thiol‐grafted cellulose paper, used as a paper strip, effects the red...

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Veröffentlicht in:Angewandte Chemie International Edition 2016-10, Vol.55 (43), p.13549-13552
Hauptverfasser: Rull-Barrull, Jordi, d'Halluin, Martin, Le Grognec, Erwan, Felpin, François-Xavier
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Sprache:eng
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Zusammenfassung:A new approach exploiting the dual properties of thiol‐grafted cellulose paper for promoting copper‐catalyzed [3+2]‐cycloadditions of organic azides with alkynes and adsorbing residual copper species in solution was developed. The thiol‐grafted cellulose paper, used as a paper strip, effects the reduction of CuII to catalytically active CuI and acts as a powerful adsorbent for copper, thereby facilitating the work‐up process and leaving the crude mixture almost free of copper residues after a single filtration. Looks good on paper: An approach that exploits the dual properties of thiol‐grafted cellulose paper for promoting copper‐catalyzed [3+2]‐cycloaddition of organic azides with alkynes and adsorbing residual copper species in solution was developed. Thiol‐grafted cellulose paper effects the reduction of CuII to catalytically active CuI and acts as a powerful adsorbent for copper, thereby facilitating the work‐up process.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201606760