Tri(cyclohexa-2,5-dien-1-yl)silane

Synthesis of multisubstituted silanes:
In a glove box, a Schlenk tube is charged with an alkene (0.300 mmol). In two vials are weighed B(C₆F₅)₃ (7.7 mg, 15 µmol) and tri(cyclohexa-2,5-dien-1-yl)silane (1, 28.0 mg, 0.105 mmol). All the sealed containers are taken out of the glove box, and the Schlenk tube is connected to a N₂ line. Under a N₂ counterflow are subsequently added 0.3 mL of CH₂Cl₂, 1 then B(C₆F₅)₃. The tube is completely sealed and stirred at room temperature for 24 h. After this time, two drops of triethylamine are added to the solution under an N₂ counterflow, and the resulting mixture is stirred for 5 min before being filtered over a short alumina column (elution with CH₂Cl₂). After evaporation of all volatiles, the crude product is purified by flash column chromatography to give the multisubstituted silane 3.