Short-RInChIKey=SA-FUHFF-UHFFFADPSC-FMKQWNTZHA-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Under an argon atmosphere, tetrakis(4-bromophenyl)methane (4.00 g, 6.29 mmol, 1.00 equiv), copper(I) iodide (120 mg, 629 μmol, 0.100 equiv) and bis(triphenylphosphine)palladium(II) dichloride (441 mg, 629 μmol, 0.100 equiv) were placed in 50 mL of degassed diisopropylamine (50 mL). Ethynyl(trimethyl)silane (8.65 g, 12.5 mL, 88.0 mmol, 14.0 equiv) was added and the reaction mixture was stirred at 80 °C for 3 d. The reaction micture was filtered over silica with dichloromethane and the solvent was removed under reduced pressure. The crude residue was purified via column chromatography (n-hexane, neutral aluminium oxide). Recrystallization from n-pentane yielded tetrakis(4-(trimethylsilylethynyl)phenyl)methane (4.24 g, 6.01 mmol, 96% yield) as an off-white solid.