Sustainable Click Reaction Catalyzed by Supported Ionic Liquid Catalyst (Cu-SILC)

Since all reactions were carried out in the presence of 1.2 equiv of triethylamine, all footnotes and Reference 21 should be revised as follows.Table 1. a Reaction was carried out at r.t. in 50% aq EtOH with 0.05 equiv of Cu-SILC and 1.2 equiv of triethylamine, in which the CuBr˙SMe2 (Cu loading: 0.18 mmol/g) was immobilized with the aid of [bmim]NTf2. Table 2. a Reaction was carried out at r.t. with 0.05 equiv of Cu-SILC and 1.2 equiv of triethylamine, in which the CuBr˙SMe2 (Cu loading: 0.18 mmol/g) was immobilized on NDEAP-silica with the aid of [bmim]NTf2.Table 3. a Reaction was carried out at r.t. in 50% EtOH with 0.05 equiv of Cu-SILC and 1.2 equiv of triethylamine, in which copper salts (Cu loading: 0.18 mmol/g) were immobilized on mercaptopropyl SiO2 with the aid of [bmim]PF6.Table 4. a Reaction was carried out at r.t. in 50% EtOH with 0.05 equiv of Cu-SILC and 1.2 equiv of triethylamine, in which the CuBr˙SMe2 was immobilized on mercaptopropyl SiO2 with the aid of [bmim]NTf2.Table 5. a Reaction was carried out at r.t. in 50% aq EtOH with 0.07 ˜ 0.08 equiv of Cu-SILC and 1.2 equiv of triethylamine, in which the CuBr˙SMe2 was immobilized on mercaptopropyl SiO2 with the aid of [bmim]PF6.Table 6. a Reaction was carried out at r.t. in 50% aq EtOH with 0.05 ˜ 0.08 equiv of Cu-SILC and 1.2 equiv of triethylamine, which was prepared from the CuBr˙SMe2.Reference 21:Click Reaction of Benzylazide and 2-Methylbut-3-yn-2-ol: A suspension of benzylazide (65 mg, 0.49 mmol), 2-methylbut-3-yn-2-ol (51 mg, 0.61 mmol), triethylamine (84 mL, 0.6 mmol) and Cu-SILC (299 mg, 0.035 mmol of CuBr) in 50% aq EtOH (2 mL) was stirred at r.t. for 2 h. The organic layer was separated by filtration and the flask was rinsed with Et2O. Combined organic layer was evaporated to dryness in vacuo. The residue was purified by column chromatography (eluent: n-hexane-ethyl acetate = 3:1 to 1:5) to give 2-[1-benzyl-1,2,3-triazol-4-yl]propan-2-ol 3a (96 mg, 91%). Recovered Cu-SILC was used intact for further recycle experiments.