p-Diiodobenzene → (4-Iodophenylethynyl)trimethylsilane

Participants

Reaction Conditions

Reaction Steps

To a mixture of (trimethylsilyl)-acetylene (2.0 mL, 14 mmol) and 1,4-diiodobenzene (9.4 g, 28 mmol) in freshly distilled TEA (40 mL) and THF (20 mL) in a 100 mL Schlenk flask were added CuI (0.19 g, 1.0 mmol) and PdCl2(PPh3)2 (0.30 g, 0.43 mmol) with stirring. The flask was then evacuated and purged with argon (3 times) on a Schlenk line. The mixture was heated at 40° C. (oil bath), sealed and stirred for 4 h. The solvents were removed under reduced pressure. The residue was dissolved in ethyl ether (150 mL), washed with H2O (3×100 mL), dried (MgSO4) and filtered. The solvent removed under reduced pressure. The resulting residue was purified by column chromatography (silica, petroleum ether/ethyl ether, 10:1) to afford 5.5 g (85%) of an off-white solid. mp 57-59° C. (lit.25 56-58° C.); 1H NMR δ 0.33 (s, 9H), 7.18, 7.64 (AA′BB′, J=8.7 Hz, 2×2H); 13C NMR δ 0.24, 94.2, 96.1, 102.6, 123.4, 133.5, 137.8; FAB-MS obsd 299.9821, calcd exact mass 299.9882 (C11H13ISi).

Provenance & Evidence