Design and Applications of an Efficient Amphiphilic “Click” CuI Catalyst in Water

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• 作者：Changlong Wang ; Dong Wang ; Shilin Yu ; Thomas Cornilleau ; Jaime Ruiz ; Lionel Salmon ; Didier Astruc
• 刊名：ACS Catalysis
• 出版年：2016
• 出版时间：August 5, 2016
• 年：2016
• 卷：6
• 期：8
• 页码：5424-5431
• 全文大小：551K
• 年卷期：0
• ISSN：2155-5435

文摘

The copper(I)-catalyzed azide alkyne cycloaddition (CuAAC) using the conventional Sharpless–Fokin catalyst that consists of CuSO₄ + Na ascorbate, the most well-known and used “click” reaction, is considerably accelerated by the addition of a tris(triazolyl)-poly(ethylene glycol) (tris-trz-PEG) amphiphilic ligand in water under ambient conditions. Only parts per million amount of Cu^I were necessary to reach quantitative yields with TONs up to 86000 and TOFs of 3600 h^–1. The ligand was fully recycled, and the catalyst was reused at least six times without decomposition. Large-scale syntheses were also successfully achieved with 93% yield. The catalyst was applied to the efficient synthesis of various useful functional products with medicinal, catalytic, targeting, and labeling properties.