Reaction Steps
In an oven-dried round-bottom flask equipped with a stir bar and cooled under N2, (3,3,4,4,5,5,6,6,7,7,8,8,9,10,10,10-hexadecafluoro-9-trifluoromethyldecyl)diisopropylsilane (4.86 g, 7.94 mmol) was dissolved in 10 mL anhydrous benzene (benzene dried by boiling off 10% by volume prior to use). To this mixture was added allyl bromide (1.44 g, 11.9 mmol, 1.5 eq.) and PdCl2 (30 mg). The solution was heated to 60° C. for 15 hr, then cooled, and concentrated via rotary evaporation. The resulting suspension was dissolved in pentane, filtered to remove residual catalyst, and then solvent was removed to yield ((3,3,4,4,5,5,6,6,7,7,8,8,9,10,10,10-hexadecafluoro-9-trifluoromethyldecyl)diisopropylsilyl)-bromide (11.3 g) as a pale brown liquid. The bromide was treated under anhydrous conditions with 1.2 eq. (based on initial silane) of ethynylmagnesium bromide and heated to 40° C. for 6 hr. The reaction was quenched with water and dilute sulfuric acid, pentane was added, and the organic layer was separated. The organic layer was washed with water (6×50 mL), dried over MgSO4, filtered, and concentrated via rotary evaporation. Further purification via flash chromatography using hexane yielded pure ((3,3,4,4,5,5,6,6,7,7,8,8,9,10,10,10-hexadecafluoro-9-trifluoromethyldecyl)diisopropylsilyl)-acetylene (4.1 g, 6.5 mmol, 82%) as a colorless liquid. Analysis of the product provided the following data: 1H-NMR (200 MHz, CDCl3) δ=2.4 (s, 1H), 2.2 (m, 2H), 1.0 (m, 14H), 0.8 (m, 2H).
