(Phenyl-4-carbonitrile)-1H-5-methylpyrazole-3-triazene resin (250 mg, 126 μmol, 1.00 equiv; 0.504 mmol/g, loading from mass difference; 0.660 mmol/g for quantitative conversion and 100% yield) was suspended in methylene chloride (3.00 mL). The suspension was cooled to 0 °C and azido(trimethyl)silane (145 mg, 167 μL, 1.26 mmol, 10.0 equiv) and 2,2,2-trifluoroacetic acid (144 mg, 96.5 μL, 1.26 mmol, 10.0 equiv) were added. The reaction mixture was slowly warmed to 50 °C and shaken for 16 hours. For the next step THF (3.00 mL) and water (3.00 mL) (1:1) was added as solvent and copper sulfate (6.03 mg, 37.8 μmol, 0.300 equiv), sodium ascorbate (25.0 mg, 126 μmol, 1.00 equiv) and ethynylbenzene (64.3 mg, 69.2 μL, 630 μmol, 5.00 equiv) were added. The reaction mixture was shaken at 50 °C for 16 hours. For work up, the reaction mixture was diluted in water and extracted three times with methylene chloride. The combined organic phase was washed with water and brine, dried over Na2SO4 and filtered.
