Compound 5

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InChIKey MGXZLISGEHFVJW-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 (N,N-Bis(diphenylphosphino)methylamine) bis(chlorogold) (5b) (100 mg, 0.12 mmol, 1.0 equiv) in THF (2 mL) was added 4-F-C₆H₄MgBr (0.66 M in THF, 1.1 mL, 0.72 mmol, 6.0 equiv) dropwise with stirring over 10 min. 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. The residue was recrystallized from CH₂Cl₂/Et₂O to yield 5 as a white powder (110 mg, 93 %). Crystals suitable for X-ray diffraction were grown by vapor diffusion of hexane vapors into a saturated 1,2-dichloroethane solution. ¹H NMR (CD₂Cl₂, 500 MHz, δ): 7.78¬ – 7.75 (m, 8H), 7.67 – 7.60 (m, 12H), 7.19 (d, J = 7.5 Hz, 4H), 6.78 (d, J = 9 Hz, 4H), 2.48 (t, J = 7.0 Hz, 3H). ¹³C{¹H} NMR (CD₂Cl₂, 125 MHz, δ): 165.4 (d, J = 125 Hz), 161.2 (d, J = 241.5 Hz), 140.7 (d, J = 5.3 Hz), 133.3 (t, J = 7.7 Hz), 132.0, 131.5 (t, J = 26.7 Hz), 129.2 (t, J = 5.4 Hz), 113.2 (d, J = 17.4 Hz), 35.2 (t, J = 3.5 Hz). ³¹P{¹H} NMR (CD₂Cl₂, 202 MHz, δ): 97.3 (s). ¹⁹F NMR (CD₂Cl_2, 470 MHz, δ): –118.0 (s). Anal. Calcd. for C₃₇H₃₁F₂Au₂NP₂: C, 45.18; H, 3.18; N, 1.42. Found: C, 44.79; H, 3.03; N, 1.37. Melting Point: 135 ºC (decomposition).