An efficient catalytic system based on 7,8-dihydroxy-4-methylcoumarin and copper(II) for the click synthesis of diverse 1,4-disubstituted-1,2,3-triazoles under green conditions

• DOI: 10.1007/s11030-014-9527-5
• Publication Date: 2014-05-27T02:25:50Z
• Authors: Hashem Sharghi; Pezhman Shiri; Mahdi Aberi
• Keywords: Sonication; Coumarins; Water; Click Chemistry; Green Chemistry Technology; Triazoles; 01 natural sciences; Catalysis; Copper; 3. Good health; 0104 chemical sciences

In this work, the combination of 7,8-dihydroxy-4-methyl coumarin (DHMC) as a novel bidentate O,O-chelating agent and copper(II) acetate monohydrate (2:1 molar ratio) has been found to form an efficient catalytic system. This catalyst provided good to excellent yields in the multi-component click synthesis of 1,4-disubstituted-1,2,3-triazoles by using various structurally diverse organic halides, different non-activated terminal alkynes, and sodium azide. This catalytic system eliminates the need for the isolation of the hazardous azide intermediates which are generated in situ. The reaction is carried out in aqueous phase at room temperature and it can be accelerated by sonication or by increasing the reaction temperature. Moreover, the reaction can be performed in large scale. It is noteworthy that DHMC is commercially available and that it can be easily synthesized with low cost materials.