An efficient method for the preparation of 1,4-disubstituted 1,2,3-triazole compounds is described using polymeric quaternary ammonium salts having azide or alkyne functionality to remove unreacted excess starting molecules (azide/alkyne). Copper metal could easily be removed by simple filtration with a short Na2SO4/silica cartridge, affording highly regioselective products in high yield and excellent purity without the need for work-up, extraction and chromatographic purification.
Triazole derivatives R 0280 Ionic Polymer-Supported Copper(I): A Reusable Catalyst for Huisgen's 1,3-Dipolar Cycloaddition. -PSCU is found to be the optimal catalyst under the conditions shown. It is remarkably stable and can be reused up to 10 times without loss of activity. -(SIRION, U.; BAE, Y. J.; LEE, B. S.; CHI*, D. Y.; Synlett 2008, 15, 2326-2330; Dep. Chem., Inha Univ., Incheon 402-751, S. Korea; Eng.) -Mais 04-123
A series of CuI-immobilized polymeric supports having quaternary ammonium salts were prepared as recyclable heterogeneous catalysts with evaluation of their ability in Cu(I)-catalyzed Huisgen's 1,3-dipolar cycloaddition of azides and terminal alkynes, a 'click reaction'. An ionic polymer possessing an acetate anion was suitable as the solid support for immobilization of CuI and CuI-immobilized compound showed negligible leaching levels of CuI, providing 1,4-disubstituted 1,2,3-triazoles in good yields, regioselectively. The CuI-immobilized compound was also reused not only up to ten times without any loss of yield or catalytic activity, but also for twelve different click reactions.
A general procedure for the high throughput synthesis of 1,4‐disubstituted 1,2,3‐triazoles under optimized reaction conditions without conventional purification is developed.
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