4-(Trimethylsilyl)phenylboronic Acid (contains varying amounts of Anhydride) → HCID 21113560, compound

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Reaction Steps

1,3,6,8-Tetrachloro-pyrene (3.50 g, 0.0103 mol), 4-trimethylsilylphenylboronic acid (10.0 g, 0.0515 mol), tris(dibenzylideneacetone)dipalladium(0) (1.18 g, 0.00129 mol), di-tert-butyl-trimethylsilylmethyl-phosphane (0.72 g, 0.0031 mol), cesium carbonate (16.78 g, 0.0515 mol) and dioxane (100 ml) were stirred at room temperature for 24 hours. The resultant mixture was poured into 200 ml of water and extracted twice with 200 ml of methylene chloride. The organic phase was dried over magnesium sulfate overnight and filtered. The solvent was removed on a roto-evaporator and the residue was purified by chromatography on silica gel with petroleum ether/ethyl ether (10/0.5) as eluent. Yield of 1,3,6,8-tetrakis-(4-trimethylsilanyl-phenyl)-pyrene was 2.39 g (29.11%) as a yellow solid with no m.p. below 250° C. 1H NMR (CD2Cl2) 0.15 (s., 36H, Me), 7.40–7.60 (br., 22H, arom-H), 7.91 (s., 2H, arom.-H), 8.20 (s., 4H, arom.-H). LC/MS: exact mass calculated for C52H58Si4: 794.36. Found: 794.36. The structure was confirmed by X-ray analysis.

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