Preparation method of axially chiral biaryl phosphine oxide and axially chiral biaryl phosphine
A biaryl and axial chirality technology, which is applied in chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, organic chemistry, etc., can solve the problems of many synthesis steps, large dosage and high cost, and avoid The effect of many steps, simple operation and high synthesis efficiency
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[0020] Example 1: Compound Preparation
[0021]
[0022] Under the protection of nitrogen, 103mg (0.25mmol) (1-bromo-2-naphthyl)-diphenylphosphine oxide, 68mg (0.5mmol) 2-methylphenylboronic acid, 159mg (0.75mmol) K 3 PO 4 , 5.77mg (0.012mmol) ligand L1, 4.58mg (0.005mmol) Pd 2 (dab) 3 Add to reaction tube. 3mL of anhydrous oxygen-free toluene was used as the solvent, and reacted at 100°C for 72 hours. The reaction system was filtered to remove insoluble matter, concentrated, and the crude product was separated and purified by a silica gel column to obtain a pale yellow solid (racemate). Yield: 80%. Enantioselectivity 67%ee (high performance liquid chromatography, Chiralcel OD-H column, 25℃, n-hexane:isopropanol=90:10, 0.5mL / min, 230nm, t R = 13.71min, 15.62min). [α] 25 D -0.8(c=5.0,CHCl 3 ), ESI-MS:419.3[M+H] + .
[0023] 1 H NMR(300MHz, CDCl 3 )δ7.88(dd,J=8.6,2.9Hz,2H),7.72(dd,J=11.5,8.5Hz,1H),7.58-7.20(m,13H),7.14-7.09(m,1H),6.92 (d,J=7.4Hz,1H),6.89(d,J=7.1Hz,1H),6.83(d,J=7...
Example Embodiment
[0041] Example 5: Compound Preparation
[0042]
[0043] Under the protection of nitrogen, 47.6mg (0.1mmol) (1-trifluoromethanesulfonate-2-naphthyl)-diphenylphosphine oxide, 40.0mg (0.2mmol) 2-biphenylboronic acid, 64mg ( 0.3mmol) K 3 PO 4 , 3.6mg (0.0048mmol) ligand L2, 1.8mg (0.002mmol) Pd(OAc) 2 Add to reaction tube. 2mL anhydrous and oxygen-free tetrahydrofuran is used as the solvent, and react at 70°C for 24-120 hours. The reaction system was filtered to remove insoluble matter, concentrated, and the crude product was separated and purified by a silica gel column to obtain a pale yellow solid. Yield: 46%. Enantioselectivity 65%ee (high performance liquid chromatography, Chiralcel OD-H column, 25℃, n-hexane:isopropanol=75:25, 1.0mL / min, 230nm, t R =7.35min, 10.42min). [α] 25 D -14.8(c=1.0,CHCl 3 ), ESI-MS:503.3[M+Na] + .
[0044] 1 H NMR(300MHz, CDCl 3 )δ7.76(d,J=8.4Hz,1H),7.71(d,J=8.17Hz,1H),7.32-7.50(m,15H),7.12-7.19(m,4H),686-6.97(m ,4H)ppm;
[0045] 13 C NMR(75MHz, CDC...
Example Embodiment
[0047] Example 6: Compound Preparation
[0048] The method steps are the same as in Example 5, the yield: 50%, the enantioselectivity is 25%ee (high performance liquid chromatography, Chiralcel OD-H column, 25℃, n-hexane:isopropanol=75:25, 1.0mL / min , 230nm, t R =17.35min, 20.46min). [α] 25 D -8.8(c=1.0,CHCl 3 ), ESI-MS:503.3[M+Na] + .
[0049] 1 H NMR(300MHz, CDCl 3 )δ 6.73-6.80 (m, 2H), 6.84-6.87 (m, 4H), 6.95-6.99 (m, 4H), 7.04-7.10 (m, 1H), 7.18-7.39 (m, 8H), 7.49- 7.55 (m, 1H), 7.60-7.69 (m, 5H) ppm;
[0050] 31 P NMR(121MHz, CDCl 3 )δ28.83ppm.
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