Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 136, Issue 34, Pages 12092-12098Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja5061388
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Funding
- Universite de Bordeaux
- CNRS
- Ministere de l'Enseignement Superieur et de la Recherche
- L'Oreal
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Upon catalyst and substrate encapsulation, an amphiphilic dendrimer containing 27 triethylene glycol termini and 9 intradendritic triazole rings serves as a catalytic nanoreactor by considerably accelerating the Cu-I-catalyzed alkyne-azide cycloaddition (CuAAC) click reactions of various substrates in water using the catalyst Cu(hexabenzyltren)Br (tren = triaminoethylamine). Moreover this recyclable nanoreactor with intradendritic triazole rings strongly also activates the simple Sharpless-Fokin catalyst CuSO4 + sodium ascorbate in water under ambient conditions leading to exceptional TONs up to 510 000. This fully recyclable catalytic nanoreactor allows to considerably decrease the amount of this cheap copper catalyst down to industrially tolerable residues, and some biomedical and cosmetic applications are exemplified.
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