Styrene → HCID 102367693, compound

Participants

Reaction Conditions

Reaction Steps

EtOH as Solvent: A solution of 1 (10.0 mg, 0.0315 mmol) in 0.4 mL of 95% aqueous ethanol was added dropwise to a solution of styrene (6.5 mg, 0.062 mmol) and palladium(II) acetate (0.5 mg, 0.002 mmol) in 0.11 g of 95% aqueous ethanol. The reaction mixture was heated by an oil bath at 70° C. for 15 h. After cooling, the mixture was filtered through a pad of Celite 545 and purified by SiO2 column chromatography (9:1 hexane/CH2Cl2) to give 2a (7.4 mg, 77% yield) as colorless crystals; m.p. 121.6-122.0° C. IR (ATR): {tilde over (v)}=3028, 1593, 1499, 1450, 1096, 964 cm−1. MS (GC, EI): m/z=306 [M+], 179. 1H NMR (500 MHz, CDCl3): δ=7.73 (d, J=8.5 Hz, 2H), 7.56 (d, J=8.5 Hz, 2H), 7.53 (d, J=7.4 Hz, 2H), 7.39 (t, J=7.4 Hz, 2H), 7.31 (t, J=7.4 Hz, 1H), 7.19 (d, J=16.4 Hz, 1H), 7.09 (d, J=16.4 Hz, 1H) ppm. 13C NMR (125 MHz, CDCl3): δ=152.5 (C), 140.6 (C), 136.4 (C), 132.0 (CH), 128.8 (2CH), 128.5 (CH), 126.8 (2CH), 126.3 (5CH) ppm. 19F NMR (470 MHz, CDCl3): δ=89.9 (quint, J=150.2 Hz, 1 F), 61.0 (d, J=150.2 Hz, 4 F) ppm.

Provenance & Evidence