Page 9 of 15
The Journal of Organic Chemistry
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(ddd, J = 17.9, 11.3, 2.4 Hz, 1H); 13C{1H} NMR (CDCl3, 125 MHz): δ 195.3 (d, JC-P = 13.6 Hz), 163.8, 136.2
(d, JC-P = 5.4 Hz), 132.2 (d, JC-P = 2.7 Hz), 131.9 (d, JC-P = 99.9 Hz), 131.6 (d, JC-P = 94.5 Hz), 131.5 (d, JC-P
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2.7 Hz), 131.5 (d, JC-P = 8.2 Hz), 131.1 (d, JC-P = 9.1 Hz), 130.6, 130.0 (d, JC-P = 5.4 Hz), 129.7, 129.1 (d, JC-P
= 11.8 Hz), 128.4 (d, JC-P = 2.7 Hz), 128.2 (d, JC-P = 11.8 Hz), 127.2 (d, JC-P = 2.7 Hz), 113.8, 55.6, 41.3 (d, JC-P
= 69.0 Hz), 38.7; 31P{1H} NMR (CDCl3, 202 MHz): δ 34.6; HRMS (ESI-TOF) m/z: [M+Na]+ calcd for
C28H25O3PNa+ 463.1434; found 463.1431. Known compound.17c
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1-(4-Acetylphenyl)-3-(diphenylphosphoryl)-3-phenylpropan-1-one 3h. 84% yield, 114 mg; white solid; mp
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208.5-209.0 °C; H NMR (CDCl3, 500 MHz): δ 7.99-7.95 (m, 2H), 7.95-7.88 (m, 4H), 7.52-7.50 (m, 2H),
7.47-7.43 (m, 2H), 7.36-7.32 (m, 4H), 7.25-7.21 (m, 2H), 7.14-7.07 (m, 3H), 4.44 (ddd, J = 9.8, 2.4, 2.4 Hz,
1H), 4.02 (ddd, J = 18.1, 10.3, 4.9 Hz, 1H), 3.41 (ddd, J = 18.1, 11.0, 2.4 Hz, 1H), 2.57 (s, 3H); 13C{1H} NMR
(CDCl3, 125 MHz): δ 197.5, 196.6 (d, JC-P = 12.7 Hz), 140.4, 139.6, 135.8 (d, JC-P = 5.4 Hz), 132.3 (d, JC-P = 2.7
Hz), 131.7 (d, JC-P = 2.7 Hz), 131.5 (d, JC-P = 100.8 Hz), 131.4 (d, JC-P = 9.1 Hz), 131.3 (d, JC-P = 93.8 Hz),
131.1 (d, JC-P = 9.1 Hz), 130.9 (d, JC-P = 11.5 Hz), 129.9 (d, JC-P = 5.4 Hz), 129.1 (d, JC-P = 10.9 Hz), 128.5 (d,
JC-P = 1.8 Hz), 128.5 (d, JC-P = 9.1 Hz), 128.3 (d, JC-P = 11.8 Hz), 127.3 (d, JC-P = 2.7 Hz), 41.3 (d, JC-P = 69.0
Hz), 39.5, 27.0; 31P{1H} NMR (CDCl3, 202 MHz): δ 34.3; IR (film) υmax: 3357, 3059, 2920, 1686, 1177, 1033
cm-1; HRMS (ESI-TOF) m/z: [M+Na]+ calcd for C29H25O3PNa+ 475.1434; found 475.1433.
3-(Diphenylphosphoryl)-3-phenyl-1-(4-(trifluoromethyl)phenyl)propan-1-one 3i. 69% yield, 99 mg; white
solid; mp 235.1-236.0 °C; 1H NMR (CDCl3, 500 MHz): δ 8.00-7.96 (m, 2H), 7.91 (d, J = 8.2 Hz, 2H), 7.62 (d,
J = 9.0 Hz, 2H), 7.55-7.44 (m, 5H), 7.37-7.32 (m, 3H), 7.26-7.22 (m, 2H), 7.15 (t, J = 7.0 Hz, 2H), 7.11-7.08
(m, 1H), 4.44 (ddd, J = 9.9, 2.6, 2.6 Hz, 1H), 4.00 (ddd, J = 18.1, 10.2, 4.9 Hz, 1H), 3.43 (ddd, J = 18.1, 11.0,
2.9 Hz, 1H); 13C{1H} NMR (CDCl3, 125 MHz): δ 196.2 (d, JC-P = 13.6 Hz), 139.2, 135.9 (d, JC-P = 5.4 Hz),
134.7 (dd, JC-F = 65.2 Hz, JC-P = 32.5Hz), 132.3 (d, JC-P = 2.7 Hz), 131.7 (d, JC-P = 2.7 Hz), 131.6 (d, JC-P = 100.8
Hz), 131.5 (d, JC-P = 95.4 Hz), 131.5 (d, JC-P = 9.1 Hz), 131.2 (d, JC-P = 9.1 Hz), 129.9 (d, JC-P = 6.4 Hz), 129.2
(d, JC-P = 10.9 Hz), 128.6, 128.6 (d, JC-P = 1.8 Hz), 128.3 (d, JC-P = 11.8 Hz), 127.4 (d, JC-P = 2.7 Hz), 125.8 (dd,
JC-F = 8.1 Hz, JC-P = 3.6 Hz), 123.6 (d, JC-F = 273.4 Hz), 41.4 (d, JC-P = 69.0 Hz), 39.5; 31P{1H} NMR (CDCl3,
202 MHz): δ 33.4; IR (film) υmax: 3056, 2920, 1692, 1177, 1130 cm-1; HRMS (ESI-TOF) m/z: [M+H]+ calcd
for C28H22F3O2PH+ 479.1382; found 479.1389.
4-(3-(Diphenylphosphoryl)-3-phenylpropanoyl)-N-methylbenzamide 3j. 60% yield, 84 mg; pale yellow
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solid; mp 122.3-124.6 °C; H NMR (CDCl3, 500 MHz): δ 7.86-7.82 (m, 2H), 7.70-7.69 (d, J = 8.3 Hz, 2H),
7.59-7.57 (d, J = 7.8 Hz, 2H), 7.38-7.33 (m, 6H), 7.23-7.20 (m, 2H), 7.19 (s, 1H), 7.09-7.06 (m, 2H), 6.97-6.92
(m, 3H),4.36 (ddd, J = 9.7, 7.0, 3.0 Hz, 1H), 3.80 (ddd, J = 16.7, 9.8, 4.7 Hz, 1H), 3.25 (ddd, J = 18.8, 11.6, 2.6
Hz, 1H), 2.82 (d, J = 4.6 Hz, 3H); 13C{1H} NMR (CDCl3, 125 MHz): δ 196.4 (d, JC-P = 12.7 Hz), 167.4, 138.8,
138.2, 135.7 (d, JC-P = 5.4 Hz), 132.4, 131.8, 131.3 (d, JC-P = 9.1 Hz), 131.2 (d, JC-P = 100.8 Hz), 131.1 (d, JC-P
= 94.5 Hz), 131.1 (d, JC-P = 9.1 Hz), 129.9 (d, JC-P = 5.4 Hz), 129.2 (d, JC-P = 10.9 Hz), 128.5, 128.3 (d, JC-P
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11.8 Hz), 128.2, 127.6, 127.3 (d, JC-P = 1.8 Hz), 41.2 (d, JC-P = 69.0 Hz), 39.1; 31P{1H} NMR (CDCl3, 202
MHz): δ 34.9; IR (film) υmax: 3296, 3059, 2927, 1659, 1183, 1117 cm-1; HRMS (ESI-TOF) m/z: [M+Na]+
calcd for C29H26NO3PNa+ 490.1543; found 490.1544.
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3-(Diphenylphosphoryl)-1-phenyl-3-(p-tolyl)propan-1-one 3k. 80% yield, 102 mg; white solid; H NMR
(CDCl3, 500 MHz): δ 7.93-7.89 (m, 2H), 7.77 (d, J = 8.0 Hz, 2H), 7.45-7.40 (m, 6H), 7.31-7.26 (m, 3H),
7.21-7.17 (m, 4H), 6.88 (d, J = 7.8 Hz, 2H), 4.41 (ddd, J = 9.8, 2.2, 2.2 Hz, 1H), 3.93 (ddd, J = 18.0, 10.4, 4.4
Hz, 1H), 3.30 (ddd, J = 18.1, 11.2, 2.3 Hz, 1H), 2.13 (s, 3H); 13C{1H} NMR (CDCl3, 125 MHz): δ 196.9 (d, JC-P
= 13.6 Hz), 136.8 (d, JC-P = 2.7 Hz), 136.6, 133.5, 132.8 (d, JC-P = 5.5 Hz), 132.1 (d, JC-P = 2.7 Hz), 131.9 (d,
JC-P = 98.6 Hz), 131.8 (d, JC-P = 95.4 Hz), 131.6 (d, JC-P = 2.7 Hz), 131.4 (d, JC-P = 9.1 Hz), 131.2 (d, JC-P = 9.1
Hz), 129.8 (d, JC-P = 5.5 Hz), 129.2 (d, JC-P = 1.8 Hz), 129.1 (d, JC-P = 11.8 Hz), 128.7, 128.3, 128.2 (d, JC-P
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