Compound 11

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InChIKey DKGWUWUYBQXKHG-UHFFFAOYSA-N

Compound data: CIF

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

To a cold (¬–78 ºC) suspension of dppp(AuCl)₂ (11a) (66.7 mg, 0.076 mmol, 1.00 equiv) in THF (5 mL) was added 4-F-C₆H₄MgBr (0.37 M in THF, 2.2 mL, 0.80 mmol, 5.7 equiv) dropwise with stirring. The reaction mixture was stirred at –78 ºC for 30 min, then warmed to 0 ºC and stirred for 1 h. The reaction was quenched at 0 ºC with sat. aq. NH₄Cl and benzene (5 mL) was added. The layers were quickly separated and the aqueous layer was washed with additional benzene (2 x 5 mL). The combined organics were dried over MgSO₄, filtered, and concentrated to dryness in vacuo to yield 11 (55 mg, 72 %). Crystals suitable for X-ray diffraction were grown by layering hexanes onto a saturated solution in CH₂Cl₂. ¹H NMR (CD₂Cl₂, 500 MHz, δ): 7.76 – 7.72 (m, 8H), 7.49 – 7.43 (m, 12H), 7.41 – 7.39 (m, 4H), 6.88 (t, J = 9.5 Hz, 4H), 3.06 ¬– 3.01 (m, 4H), 2.00 ¬– 1.91 (m, 2H). ¹³C{¹H} NMR (CD₂Cl₂, 125 MHz, δ): 168.4 (d, J_C-P = 125.0 Hz), 162.0 (d, J_C-F = 237.5 Hz), 141.0 (d, J = 5.4 Hz), 134.1 (d, J = 13.8 Hz), 131.8, 131.4, 129.6 (d, J = 10.0 Hz), 114.1 (dd, J = 17.5 Hz, 6.3 Hz), 28.8 (dd, J = 28.8 Hz, 8.8 Hz), 19.9. ³¹P{¹H} NMR (CD₂Cl₂, 202 MHz, δ): 34.0 (s). ¹⁹F NMR (CD₂Cl₂, 470 MHz, δ): –117.3 (s). Anal. Calcd. for C₃₉H₃₄P₂F₂Au₂: C, 47.00; H, 3.44. Found: C, 47.19; H, 3.72. Melting point: 105 ºC (decomposition).