Practical one-pot synthesis of 5-alkynyl-1,2,3-triazoles via heterogeneous copper(I)-catalyzed tandem three-component click/alkynylation reaction |
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Authors: | Ruonan Zhao Yang Liao Tao Yan Mingzhong Cai |
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Institution: | Key Laboratory of Functional Small Organic Molecule, Ministry of Education and College of Chemistry & Chemical Engineering, Jiangxi Normal University, Nanchang, 330022 China |
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Abstract: | An efficient and practical route to 5-alkynyl-1,2,3-triazoles has been developed via heterogeneous tandem CuAAC/alkynylation reaction of organic azides, alkynes and 1-bromoalkynes by using an L-proline-functionalized MCM-41-anchored copper(I) complex L-Proline-MCM-41-CuCl] as catalyst under mild conditions. The reaction produces a wide variety of 5-alkynyl-1,2,3-triazoles in mostly good to excellent yields. The new immobilized copper(I) complex can be readily prepared from commercially available and inexpensive reagents and displays the same catalytic activity as CuCl. The L-Proline-MCM-41-CuCl catalyst is also easy to recover via a simple filtration process and can be reused at least seven times without apparent loss of activity. |
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Keywords: | 5-alkynyl-1 2 3-triazole alkynylation click reaction copper heterogeneous catalysis |
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