Y. Zhou, C. Liu, Z. Shen et al.
Journal of Organometallic Chemistry 949 (2021) 121932
(m, 1H), 8.00-8.02 (m, 1H), 8.58-8.60 (m, 1H); 13C NMR (100 MHz,
CDCl3): δ = 124.14 (d, JCP = 14 Hz, CH), 126.51 (s, CH), 127.35 (s,
CH), 127.66 (d, JCP = 6 Hz, CH), 128.59 (d, JCP = 12 Hz, 4CH), 128.77
(s, CH), 128.99 (d, JCP = 102 Hz, C), 131.89 (d, JCP = 3 Hz, 2CH),
132.11 (d, JCP = 10 Hz, 4CH), 132.92 (d, JCP = 103 Hz, 2C), 133.28 (d,
JCP = 3 Hz, CH), 133.76 (d, JCP = 11 Hz, CH), 133.78 (d, JCP = 6 Hz,
C), 133.94 (d, JCP = 9 Hz, C); HRMS Calcd. for C22H17 OP [M + H+]
329.1095, Found: 329.1092.
134.68 (d, JCP = 13 Hz, C), 140.02 (JCP = 8 Hz, C); HRMS: Calcd. for
C20H19 OP[M + H+] 307.1252, Found: 307.1255.
7. (3, 5-Di-tert-butylphenyl)diphenylphosphine oxide (3d)
white solid (507 mg, 1.30 mmol, 65 % yield), 1H NMR (400
MHz, CDCl3) δ = 1.27 (s, 18H), 7.43-7.45 (m, 5H), 7.52-7.55 (m, 3H),
7.59-7.60 (m, 1H), 7.66-7.71 (m, 4H); 13C NMR (100 MHz, CDCl3)
δ = 31.29 (s, CH3), 35.02 (s, C), 126.06 (d, JCP = 3 Hz, CH), 126.38
(d, JCP = 10 Hz, 2CH), 128.35 (d, JCP = 12 Hz, 4CH), 131.21 (d,
JCP = 100 Hz, C), 131.74 (s, 2CH), 132.09 (d, JCP = 10 Hz, 4CH),
133.12 (d, JCP = 102 Hz, 2C), 150.99 (d, JCP = 12 Hz, 2C); HRMS:
Calcd. for C26H31OP[M + H+] 391.2191, Found: 391.2187.
13. Naphthalen-2-yldiphenylphosphine oxide (3j)
white solid (453 mg, 1.38 mmol, 69 % yield), 1H NMR (400
MHz, CDCl3) δ = 7.44-7.74 (m, 13H), 7.85-7.91 (m, 3H), 8.27 (d,
JHH = 16 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ = 126.84 (d,
JCP = 10 Hz, CH), 126.99 (s, CH), 127.85 (s, CH), 128.30 (s, CH),
126.36 (d, JCP = 11 Hz, CH), 128.58 (d, JCP = 12 Hz, 4CH), 128.99
(s, CH), 129.52 (d, JCP = 105 Hz, C), 132.01 (d, JCP = 4 Hz, 2CH),
132.16 (d, JCP = 10 Hz, 4CH), 132.45 (d, JCP = 13 Hz, C), 132.51 (d,
JCP = 103 Hz, 2C), 134.04 (d, JCP = 9 Hz, CH), 134.75 (d, JCP = 2
Hz, C); HRMS: Calcd. for C22H17 OP[M + H+] 329.1095, Found:
329.1092.
8. (4-Methoxyphenyl)diphenylphosphine oxide (3e)
white solid (480 mg, 1.56 mmol, 78 % yield), 1H NMR (400
MHz, CDCl3) δ = 3.83 (s, 3H), 6.95-6.98 (m, 2H), 7.42-7.47 (m, 4H),
7.50-7.61 (m, 4H), 7.64-7.69 (m, 4H); 13C NMR (100 MHz, CDCl3)
δ = 55.34 (s, CH3), 114.12 (d, JCP = 13 Hz, 2CH), 123.58 (d, JCP = 110
Hz, C), 128.44 (d, JCP = 12 Hz, 4CH), 131.80 (d, JCP = 3 Hz, 2CH),
132.05 (d, JCP = 10 Hz, 4CH), 133.49 (d, JCP = 104 Hz, 2C), 133.97
(d, JCP = 12 Hz, 2CH), 162.55 (d, JCP = 3 Hz, C); HRMS: Calcd. for
C19 H17 O2P[M + H+] 309.1044, Found: 309.1046.
14. Phenanthren-9-yldiphenylphosphine oxide (3k)
white solid (582 mg, 1.54 mmol, 77 % yield), 1H NMR (400
MHz, CDCl3) δ = 7.42-7.49 (m, 5H), 7.51-7.56 (m, 3H), 7.58-7.77 (m,
8H), 8.64-8.69 (m, 3H); 13C NMR (100 MHz, CDCl3) δ = 122.66 (s,
CH), 123.06 (s, CH), 127.04 (s, CH), 127.21 (d, JCP = 5 Hz, 2CH),
127.92 (d, JCP = 101 Hz, C), 128.67 (d, JCP = 12 Hz, 4CH), 128.76 (d,
JCP = 6 Hz, CH), 129.15 (s, CH), 130.06 (s, CH), 130.19 (d, JCP = 110
Hz, C), 130.19 (d, JCP = 103 Hz, C), 130.51 (d, JCP = 8 Hz, C), 131.99
(s, CH), 132.02 (s, CH), 132.18 (d, JCP = 9 Hz, CH), 132.17 (d, JCP = 9
Hz, 4CH), 133.25 (s, C), 136.80 (s, C), 136.92 (s, C); HRMS: Calcd.
for C26H19 OP[M + H+] 379.1252, Found: 379.1253.
9. (2, 5-Dimethoxyphenyl)diphenylphosphine oxide (3f)
white solid (534 mg, 1.58 mmol, 79 % yield), 1H NMR (400
MHz, CDCl3) δ = 3.45 (s, 3H), 3.79 (s, 3H), 6.84-6.87 (m, 1H), 7.05-
7.08 (m, 1H), 7.40-7.44 (m, 7H), 7.69-7.74 (m, 4H); 13C NMR (100
MHz, CDCl3) δ = 55.79 (s, CH3), 55.94 (s, CH3), 113.18 (d, JCP = 8
Hz, CH), 118.87 (d, JCP = 4 Hz, CH), 120.35 (d, JCP = 2 Hz, CH),
121.20 (d, JCP = 102 Hz, C), 128.09 (d, JCP = 12 Hz, 4CH), 131.50 (d,
JCP = 3 Hz, 2CH), 131.85 (d, JCP = 10 Hz, 4CH), 133.66 (d, JCP = 107
Hz, 2C), 153.90 (d, JCP = 14 Hz, C), 154.75 (d, JCP = 3 Hz, C); HRMS:
Calcd. for C20H19O3P[M + H+] 339.1150, Found: 339.1150.
15. Diphenyl(pyridin-2-yl)phosphine oxide (6a)
10. Benzo[d][1,3]dioxol-5-yldiphenylphosphine oxide (3g)
white solid (502 g, 1.80 mmol, 90 % yield), 1H NMR (400 MHz,
CDCl3) δ = 7.35-7.53 (m, 7H), 7.81-7.91 (m, 5H), 8.29-8.32 (m, 1H),
8.77 (d, JHH = 4 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ = 125.28 (d,
JCP = 3 Hz, CH), 128.35 (d, JCP = 12 Hz, 4CH), 128.37 (d, JCP = 19
Hz, CH), 131.90 (d, JCP = 2 Hz, 2CH), 132.16 (d, JCP = 9 Hz, 4CH),
132.18 (d, JCP = 104 Hz, 2C), 136.21 (d, JCP = 9 Hz, CH), 150.13 (d,
JCP = 19 Hz, CH), 156.39 (d, JCP = 131 Hz, C); HRMS: Calcd. for
C17 H14 NOP[M + H+] 280.0891, Found: 280.0895.
white solid (548 mg, 1.70 mmol, 85 % yield), 1H NMR (400
MHz, CDCl3): δ = 6.00 (s, 2H), 6.85-6.89 (m, 1H), 7.06-7.09 (m,
1H), 7.15-7.21 (m, 1H), 7.43-7.47 (m, 4H), 7.51-7.55 (m, 2H), 7.64-
7.69 (m, 4H); 13C NMR (100 MHz, CDCl3): δ = 101.62 (s, CH2),
108.64 (d, JCP = 16 Hz, CH), 111.56 (d, JCP = 12 Hz, CH), 125.73
(d, JCP = 107 Hz, C), 127.59 (d, JCP = 10 Hz, CH), 128.48 (d, JCP = 11
Hz, 4CH), 131.89 (d, JCP = 3 Hz, 2CH), 132.05 (d, JCP = 10 Hz, 4CH),
132.76 (d, JCP = 104 Hz, 2C), 148.00 (d, JCP = 18 Hz, C), 150.87 (d,
JCP = 3 Hz, C); HRMS Calcd. for C19 H15O3P [M + H+] 323.0837,
Found: 323.0839.
16. Diphenyl(quinolin-2-yl)phosphine oxide (6b)
white solid (573 g, 1.74 mmol, 87 % yield), 1H NMR (400 MHz,
CDCl3) δ = 7.41-7.51 (m, 6H), 7.56-7.60 (m, 1H), 7.70-7.74 (m, 1H),
7.82-7.84 (m, 1H), 7.97-8.03 (m, 4H), 8.14-8.16 (m, 1H), 8.27-8.31
(m, 1H), 8.35-8.37 (m, 1H); 13C NMR (100 MHz, CDCl3) δ = 123.37
(d, JCP = 22 Hz, CH), 127.89 (s, CH), 128.17 (s, CH), 128.32 (d,
JCP = 12 Hz, 4CH), 130.05 (s, CH), 130.32 (s, CH), 131.81 (d, JCP = 3
Hz, 2CH), 132.23 (d, JCP = 9 Hz, 4CH), 132.56 (d, JCP = 103 Hz, 2C),
136.17 (d, JCP = 9 Hz, CH), 148.04 (s, C), 148.25 (s, C), 157.20 (d,
JCP = 129 Hz, C); HRMS: Calcd. for C21H16 NOP[M + H+] 330.1048,
Found: 330.1043.
11. (4-Fluorophenyl)diphenylphosphine oxide (3h)
white solid (509 mg, 1.72 mmol, 86 % yield), 1H NMR (400
MHz, CDCl3) δ = 7.12-7.17 (m, 2H), 7.44-7.49 (m, 4H), 7.52-7.57
(m, 2H), 7.63-7.71 (m, 6H); 13C NMR (100 MHz, CDCl3) δ = 115.88
(dd, J1 = 21 Hz, J1 = 3 Hz, 2CH), 128.58 (d, JCP = 12 Hz, 4CH),
128.65 (dd, JCP = 106 Hz, JCF = 3 Hz, C) 132.0 (d, JCP = 10 Hz,
4CH), 132.07 (d, JCP = 4 Hz, 2CH), 132.37 (d, JCP = 104 Hz, 2C),
134.57 (dd, J1 = 11 Hz, J1 = 9 Hz, 2CH), 165.06 (dd, JCF = 252
Hz, JCP = 3 Hz, C); HRMS: Calcd. for C18 H14 FOP[M + H+] 297.0845,
Found: 297.0848.
17. 4-(Diphenylphosphino)benzoic acid (8); Procedure
12. Naphthalen-1-yldiphenylphosphine oxide (3i)
In a 250 mL schlenk bottle was stirred a mixture of 7 (4.02 g,
20 mmol), 2 (3.91 g, 21 mmol) in DMF (150 mL) under a nitrogen
atmosphere at room temperature, then, KOH (1.35 g, 24 mmol) was
added and the mixture was warmed to 110 °C and keep stirring
white solid (492 mg, 1.50 mmol, 75 % yield), 1H NMR (400
MHz, CDCl3): δ = 7.27-7.56 (m, 10H), 7.66-7.71 (m, 4H), 7.87-7.90
6