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DOI: 10.1055/s-0034-1379715
Click Reaction Using Polymer-Supported CuI–Cryptand-22
Polystyrene Resin-Supported CuI–Cryptand-22 Complex: A Highly Efficient and Reusable Catalyst for Three-Component Synthesis of 1,4-Disubstituted 1,2,3-Triazoles Under Aerobic Conditions in Water.
Tetrahedron 2014;
70: 8885-8892
Publication History
Publication Date:
15 December 2014 (online)
Significance
A polystyrene resin supported CuI–cryptand-22 complex (PS–C22–CuI) was prepared by mixing chloromethylated polystyrene with cryptand-22 in diethyl ether, followed by the complexation with CuI in ethanol (eq. 1). PS–C22–CuI catalyzed the click reaction of azides with terminal alkynes (eq. 2, method A) or the one-pot three-component reaction from alkyl halides, sodium azide, and terminal alkynes (eq. 3, method B) to give the corresponding 1,2,3-triazoles in up to 99% yield.
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Comment
The PS–C22–CuI complex was characterized by FT-IR, EDX, SEM, XPS, and TG-DTA analysis. In both methods A and B for synthesizing 1-benzyl-4-phenyl-1H-1,2,3-triazole, the catalyst was recovered by filtration and reused three times.
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