Li, Yuan & Chen
FULL PAPER
2
,2'-Dicarboxyl diphenyl sulfide (Entry 7, Table
Technology Planning Project (No. GJJ11066). We also
thank the Analysis and Testing Center of Jiangxi Nor-
mal University for NMR measurements.
[
41]
1
2
)
White solid; m.p. 198—199 ℃; H NMR (400
MHz, DMSO-d ) δ: 13.12 (s, 2H), 7.84 (d, J=7.2 Hz,
H), 7.46 (t, J=7.2 Hz, 2H), 7.38 (t, J=7.2 Hz, 2H),
6
2
7
1
3
.12 (d, J = 7.2 Hz, 2H); C NMR (100 MHz,
) δ: 167.7, 136.4, 132.9, 132.1, 132.0, 130.0,
References
DMSO-d
6
+
[1] Jones, D. N. In Comprehensive Organic Chemistry, Vol. 3, Eds.:
Barton, D. H.; Ollis, D. W., Pergamon, New York, 1979.
1
26.9; MS (EI) m/z: 274 [M ].
3
,3'-Dimethoxydiphenyl sulfide (Entry 10, Table
[
[
2] Muci, A. R.; Buchwald, L. S. Top. Curr. Chem. 2002, 219, 131.
3] Beletskaya, I. P.; Ananikov, V. P. Chem. Rev. 2011, 111, 1596.
[
38]
1
2
)
White solid; m.p. 159—161 ℃; H NMR (400
/TMS) δ: 7.24 (t, J=8.0 Hz, 2H), 6.96 (d,
J=8.0 Hz, 2H), 6.92 (s, 2H), 6.80—6.84 (m, 2H), 3.79
MHz, CDCl
3
[4] Migita, T.; Shimizu, T.; Asami, Y.; Shiobara, J.; Kato, Y.; Kosugi,
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1
3
[
[
5] Li, G. Y. Angew. Chem., Int. Ed. 2001, 40, 1513.
6] Murata, M.; Buchwald, S. L. Tetrahedron 2004, 60, 7397.
(
1
2
3
s, 6H); C NMR (100 MHz, CDCl /TMS) δ: 160.1,
36.6, 130.1, 123.4, 116.3, 113.1, 55.4; MS (EI) m/z:
46 [M ].
+
[7] Fernández-Rodríguez, M. A.; Shen, Q.; Hartwig, J. F. Chem. Eur. J.
006, 12, 7782.
2
2
,2'-Dimethoxydiphenyl sulfide (Entry 11, Table
[
[
8] Itoh, T.; Mase, T. Org. Lett. 2004, 6, 4587.
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[
38]
1
2
)
White solid; m.p. 148—150 ℃; H NMR (400
/TMS) δ: 7.31—6.89 (m, 8H), 3.91 (s, 6H);
C NMR (CDCl , 100 MHz) δ: 157.4, 132.1, 128.3,
22.6, 121.2, 110.9, 55.4; MS (EI) m/z: 246 [M ].
,3'-Dimethyldiphenyl sulfide (Entry 13, Table
MHz, CDCl
3
[10] Jammi, S.; Barua, P.; Rout, L.; Saha, P.; Punniyamurthy, T. Tetra-
hedron Lett. 2008, 49, 1484.
1
3
3
+
[
[
11] She, J.; Jiang, Z.; Wang, Y. G. Tetrahedron Lett. 2009, 50, 593.
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3
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1
[13] Reddy, V. P.; Swapna, K.; Kumar, A. V.; Rao, K. R. J. Org. Chem.
009, 74, 3189.
2
)
3
Colorless oil; H NMR (400 MHz, CDCl /TMS)
2
13
3
δ: 7.35—6.92 (m, 8H), 3.93 (s, 6H); C NMR (CDCl ,
00 MHz) δ: 137.6, 132.4, 128.5, 122.9, 121.7, 111.2,
1.8; MS (EI) m/z: 214 [M ].
3
[
14] Reddy, V. P.; Kumar, A. V.; Swapna, K.; Rao, K. R. Org. Lett. 2009,
11, 1697.
1
2
+
[15] Murthy, S. N.; Madhav, B.; Reddy, V. P. Eur. J. Org. Chem. 2009,
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[43]
5
,3'-Diflurodiphenyl sulfide (Entry 15, Table 2)
1
[16] orrea, A.; Carril, M.; Bolm, C. Angew. Chem., Int. Ed. 2008, 47,
Colorless oil; H NMR (400 MHz, CDCl
3
/TMS) δ:
, 100 MHz) δ:
63.5, 161.3, 133.7, 133.4, 131.7, 116.9, 116.8; MS (EI)
13
2880.
7
1
.23—7.41 (m, 4H); C NMR (CDCl
3
[
[
[
17] Wu, W. Y.; Wang, J. C.; Tsai, F. Y. Green Chem. 2009, 11, 326.
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19] Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248,
2337.
+
m/z: 222 [M ].
2
,2'-Dichrolodiphenyl sulfide (Entry 16, Table
[
44]
1
2
)
Colorless oil; H NMR (400 MHz, CDCl
3
/TMS)
[20] hemler, S. R.; Fuller, P. H. Chem. Soc. Rev. 2007, 36, 1153.
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[
δ: 7.62 (d, J=7.8 Hz, 2H), 7.21 (t, J=7.3 Hz, 2H), 7.12
t, J=7.5 Hz, 4H); C NMR (CDCl , 100 MHz) δ:
3
35.6, 133.2, 132.5, 128.7, 128.2, 125.6; MS (EI) m/z:
55 [M ].
13
(
1
2
[
23] Bates, C. G.; Saejueng, P.; Doherty, M. Q.; Venkataraman, D. Org.
Lett. 2004, 6, 5005.
+
[
24] Chen, Y. J.; Chen, H. H. Org. Lett. 2006, 8, 5609.
2
,2'-Dihydroxyldiphenyl sulfide (Entry 17, Table
[25] Rout, L.; Sen, T. K.; Punniyamurthy, T. Angew. Chem., Int. Ed.
2007, 46, 5583.
[
45]
1
2
)
White solid; m.p. 139—141 ℃; H NMR (400
1
3
[
26] Bhadra, S.; Sreedhar, B.; Ranu, B. C. Adv. Synth. Catal. 2009, 351,
369.
[27] Wang, H.; Jiang, L.; Chen, T.; Li, Y. Eur. J. Org. Chem. 2010, 2324.
MHz, CDCl
3
/TMS) δ: 7.26—6.85 (m, 8H); C NMR
2
(
1
CDCl , 100 MHz) δ: 156.4, 131.7, 128.1, 122.1, 120.6,
10.3; MS (EI) m/z: 218 [M ].
3
+
[
28] Kabir, M. S.; Lorenz, M.; Van-Linn, M. L. J. Org. Chem. 2010, 75,
626.
29] Duan, Z.; Ranjit, S.; Liu, X. Org. Lett. 2010, 12, 2430.
3
,3'-Dihydroxyldiphenyl sulfide (Entry 18, Table
3
[
46]
1
2
)
3
Colorless oil; H NMR (400 MHz, CDCl /TMS)
[
δ: 7.32—7.16 (m, 2H), 6.98—6.73 (m, 6H), 5.53 (bs,
[30] Chu, L.; Yue, X.; Qing, F. Org. Lett. 2010, 12, 1644.
[31] Xu, R.; Wan, J.; Mao, H.; Pan, Y. J. Am. Chem. Soc. 2010, 132,
1
3
2
1
H); C NMR (CDCl
3
, 100 MHz) δ: 156.4, 136.5,
1
5531.
[32] Luo, F.; Pan, C.; Li, L.; Chen, F.; Cheng, J. Chem. Commun. 2011,
7, 5304.
33] Firouzabadi, H.; Iranpoor, N.; Gholinejad, M. Adv. Synth. Catal.
010, 352, 119.
30.4, 128.3, 123.5, 117.6, 114.7; MS (EI) m/z: 218
+
[
M ].
4
4
,4'-Dihydroxyldiphenyl sulfide (Entry 19, Table
[
[
47]
1
2
)
White solid; m.p. 151—152 ℃; H NMR (400
/TMS) δ: 7.24—7.17 (m, 4H), 6.87—6.78
2
MHz, CDCl
m, 4H), 5.57 (bs, 2H); C NMR (CDCl
3
[34] Zhang, S.; Qian, P.; Zhang, M.; Hu, M.; Cheng, J. J. Org. Chem.
2010, 75, 6732.
1
3
(
3
, 100 MHz) δ:
[
35] Ma, D.; Xie, S.; Xue, P.; Zhang, X.; Dong, J.; Jiang, Y. Angew.
Chem., Int. Ed. 2009, 48, 4222.
1
56.5, 135.9, 130.8, 128.7, 123.8, 117.6, 114.9; MS (EI)
+
m/z: 218 [M ].
[
[
36] You, W.; Yan, X.; Liao, Q.; Xi, C. Org. Lett. 2010, 12, 3930.
37] Park, N. J.; Park, K. H.; Jang, M. H.; Lee, S. W. J. Org. Chem. 2011,
Acknowledgements
7
6, 4371.
38] Ke, F.; Qu, Y.; Jiang, Z.; Li, Z.; Wu, D.; Zhou, X. Org. Lett. 2011,
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[
[
This work was sponsored by the Jiangxi Provincial
Natural Science Foundation (No. 2010GQH0064) and
Jiangxi Provincial Educational Commission Science and
1
39] Chen, J.; Yuan, T.; Hao, W.; Cai, M. Tetrahedron Lett. 2011, 52,
3710.
654
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Chin. J. Chem. 2012, 30, 651—655