Regioselective C-S Bond Formation Accomplished by Regioselective C-F
Letters in Organic Chemistry, 2012, Vol. 9, No. 3 181
(m, 1F), -76.2 (m, 1F), -91.7 (m, 1F); MS (EI): 332 (M+);
HRMS calcd for C14H8ClF3O2S: 331.9886 found:331.9889.
125.0 (dd, J1 = 11.7 Hz, J2 = 11.8 Hz), 117.4 (m); 19F NMR
(CDCl3, 300 MHz): -112.1 (s, 2F), -115.9 (s, 2F); MS (EI):
366 (M+); HRMS calcd for C18H10F4S2: 366.0160,
found:366.0158.
1
3k: white solid; m.p. 63-64°C; H NMR (CDCl3, 400
MHz): 7.50-7.46 (m, 1H), 7.38-7.28 (m, 4H), 3.95 (s, 3H);
13C NMR (CDCl3, 100 MHz): 163.1 (t, J = 2.0 Hz), 158.5 (t,
J = 3.9 Hz), 156.1 (t, J = 3.3 Hz), 152.9 (m), 150.4 (dd, J1 =
4.6 Hz, J2 = 5.0 Hz), 148.8 (m), 146.2 (dd, J1 = 4.5 Hz, J2 =
2.0 Hz), 132.9, 131.1, 129.6, 128.3, 119.8 (dm, J = 122.2
Hz), 112.8 (dd, J1 = 4.0 Hz, J2 = 3.9 Hz), 53.2; 19F NMR
(CDCl3, 300 MHz): -110.0 (dd, J1 = 21.9 Hz, J2= 22.5 Hz,
1F), -112.6 (m, 1F), -125.6 (d, J = 23.4 Hz, 1F), -137.6 (m,
1F); MS (EI): 316 (M+); HRMS calcd for C14H8F4O2S:
316.0181, found: 316.0184.
ACKNOWLEDGEMENTS
We thank the National Natural Science Foundation of
China (No. 21172166) and Natural Science Foundation of
Zhejiang Province (Y4100783) for financial support.
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3l: colorless gel; H NMR (CDCl3, 400 MHz): 7.53-7.41
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1
3m: colorless gel; H NMR (CDCl3, 400 MHz): 7.41 (d,
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4H), 6.52 (q, J = 6.8 Hz, 1H), 4.89 (d, J = 2.0 Hz, 2H), 2.39
(s, 3H), 2.27 (s, 3H), 2.14 (s, 1H); 13C NMR (CDCl3, 100
MHz): 161.0 (d, J = 2.6 Hz), 158.5 (d, J = 2.8 Hz), 154.7,
152.3, 140.3, 137.0, 135.3, 132.3, 132.1, 131.1, 130.3, 128.7,
126.0, 118.6 (d, J = 20.0 Hz), 115.0 (d, J = 29.5 Hz), 57.2 (q,
J = 2.2 Hz), 21.5, 21.2; 19F NMR (CDCl3, 300 MHz): -80.6
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3n: colorless gel; 1H NMR (CDCl3, 400 MHz): 7.42-7.33
(m, 10H), 6.78 (t, J = 7.6 Hz, 2H); 13C NMR (CDCl3, 100
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128.5, 124.4 (dd, J1 = 12.2 Hz, J2 = 12.6 Hz), 117.8 (m); 19
F
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330 (M+); HRMS calcd for C18H12F2S2: 330.0349, found:
330.0347.
1
3o: white solid; m.p. 162-164°C; H NMR (CDCl3, 400
MHz): 7.33 (d, J = 8.0 Hz, 4H), 7.17 (d, J = 8.0 Hz, 4H),
6.68 (t, J = 7.6 Hz, 2H), 2.36 (s, 6H); 13C NMR (CDCl3, 100
MHz): 157.4 (d, J = 2.8 Hz), 155.0 (d, J = 2.7 Hz), 139.2,
133.6, 130.8, 128.2, 125.0 (dd, J1 = 12.6 Hz, J2 = 11.4 Hz),
117.2 (m), 21.5; 19F NMR (CDCl3, 300 MHz): -84.3 (t, J =
9.6 Hz, 2F); MS (EI): 358 (M+); HRMS calcd for
C20H16F2S2: 358.0662, found: 358.0662.
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1
3p: colorless gel; H NMR (CDCl3, 400 MHz): 7.33 (s,
8H), 6.80 (t, J = 7.6 Hz, 2H); 13C NMR (CDCl3, 100 MHz):
157.8 (d, J = 3.1 Hz), 155.4 (d, J = 3.6 Hz), 135.1, 134.0,
130.8, 130.2, 124.5 (dd, J1 = 12.5 Hz, J2 = 12.2 Hz), 118.3
(m); 19F NMR (CDCl3, 300 MHz): -86.0 (t, J = 7.5 Hz, 2F);
MS (EI): 398 (M+); HRMS calcd for C18H10Cl2F2S2:
397.9569, found: 397.9566.
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1
3q: white solid; m.p. 143-145°C; H NMR (CDCl3, 400
MHz): 7.45-7.42 (m, 4H), 7.08 (t, J = 8.4 Hz, 4H), 6.69 (t, J
= 7.6 Hz, 2H); 13C NMR (CDCl3, 100 MHz): 164.6, 162.2,
157.4, 155.0 (d, J = 2.9 Hz), 135.7 (d, J = 8.1 Hz), 127.0,