Synthesis of Mix-BINDFOH
In a two-necked schlenk flask (250 mL), 2,2′-Dibromo-1,1′-binaphthyl
(a1) (0.5 g, 1.2 mmol), PhFOL (1.15 g, 3 mmol),
Pd(PPh3)4 (11 mg, 0.96 mmol) were added.
The flask was evacuated and back-filled with nitrogen atmosphere over
three times, after which degassed toluene (12 mL) and
K2CO3/KF aqueous solution (4.2 M, 6 mL,
2 eq.) were injected into the flask through syringe. The mixture was
heated up to 95 ℃ and stirred for 24 hours. The mixture was extracted
three times with CH2Cl2 and the organic
layer was dried over Na2SO4, filtered
and the solvent was removed under reduced pressure. Purification by
silica gel column chromatography (petroleum ether:
CH2Cl2 = 1:3) to afford Mix-BINDFOH (0.6
g, 65%) as a white powder.
Mix-BINDFOH (yield 65%). 1H NMR (400 MHz,
CDCl3) δ 8.03‒8.01 (d, J = 8.4 Hz, 1H),
7.90–7.88 (d, J = 8.8 Hz, 1H), 7.77‒7.75 (d, J = 7.6 Hz,
1H), 7.69‒7.67 (d, J = 8.8 Hz, 1H), 7.61‒7.55 (dd, J = 7.6
Hz, 6.8 Hz, 4H), 7.49–7.47 (d, J = 7.6 Hz, 1H), 7.42–7.40 (d,J = 7.6 Hz, 2H), 7.38 ‒7.27 (m, 7H), 7.25–7.22 (m, 4H),
7.19–7.12 (m, 5H), 7.08–7.04 (t, J = 7.6 Hz, 2H), 7.00–6.96
(t, J = 7.6 Hz, 3H), 6.85–6.83 (d, J = 7.2 Hz, 2H),
6.73–6.71 (d, J = 7.6 Hz, 1H), 6.47–6.45 (d, J = 8.8 Hz,
3H), 2.39 (s, 1H), 1.87 (s, 1H). 13C NMR (100 MHz,
CDCl3) δ 149.5, 149.1, 148.0, 141.4, 140.4, 137.8,
133.3, 131.0, 130.7, 129.1, 128.8, 127.8, 127.1, 126.9, 126.8, 126.1,
125.8, 125.6, 125.4, 124.5, 124.2, 123.9, 123.7, 123.3, 118.7, 118.0,
117.8, 82.0, 81.7 ppm. MALDI-ToF-MS (m/z): calcd. For
C58H38O2: 766.29
[M+]; Found: 766.52.