6
Tetrahedron
TED
Ananikov, Chem. Rev., 2011, 111, 1596–1636; (d) T. Kondo and
T.-A. Mitsudo, Chem. Rev., 2000, 100, 3205–3220.
CDCl ): δ 161.23, 150.81, 147.17, 134.82
A
, 1
C
34
C
.6
E
5,
P
1
34
.5
0, MANUSCRIPT
3
1
2
34.41, 129.81, 129.63, 126.35, 125.58, 123.69, 111.50, 56.25,
3.04, 21.02, 20.98, 20.67.
2
.
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[
12b]
4
.25. Mesityl(p-tolyl)sulfane [3qa]
1
H NMR (400 MHz, CDCl ): δ 6.98 (d, J = 9.2 Hz, 4H), 6.82
3
13
(d, J = 8.4 Hz, 2H), 2.38 (s, 6H), 2.31 (s, 3H), 2.25 (s, 3H).
C
2
014, 16, 876–879; (e) J. T. Reeves, K. Camara, Z. S. Han, Y. Xu,
NMR (101 MHz, CDCl ): δ 143.75, 139.20, 134.89, 134.35,
3
H. Lee, C. A. Busacca and C. H. Senanayake, Org. Lett., 2014, 16,
1196–1199; (f) V. G. Pandya and S. B. Mhaske, Org. Lett., 2014,
1
29.77, 129.40, 127.58, 125.81, 21.88, 21.26, 21.00.
1
6, 3836–3839; (g) F. Xiao, H. Chen, H. Xie, S. Chen, L. Yang
[
12b]
4
.26. (4-Methoxyphenyl)(p-tolyl)sulfane [3ra]
and G. Deng, Org. Lett., 2014, 16, 50–53; (h) Y. Xu, X. Tang, W.
Hu, W. Wu and H. Jiang, Green Chem., 2014, 16, 3720–3723.
1
H NMR (400 MHz, CDCl ): δ 7.35 (d, J = 8.4 Hz, 2H), 7.13
3. N. Singh, R. Singh, D. S. Raghuvanshi, and K. Nand Singh. Org.
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3
(d, J = 8.0 Hz, 2H), 7.06 (d, J = 8.0 Hz, 2H), 6.86 (d, J = 8.8 Hz,
13
4
.
T. Wang, F. Yang, and S. Tian, Adv. Synth. Catal. 2015, 357,
28–932.
2
1
2
H), 3.80 (s, 3H), 2.29 (s, 3H). C NMR (101 MHz, CDCl ): δ
59.57, 136.23, 134.47, 129.89, 129.50, 125.76, 114.98, 55.47,
1.11.
3
9
5
.
S. Yoshida, Y. Sugimura, Y. Hazama, Y. Nishiyama, T. Yano, S.
Shimizu, and T. Hosoya. Chem. Commun., 2015, 51, 16613-
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.27. 2,3-bis(p-tolylthio)-1H-indole[3sb]
6
.
P. Saravanan , P. Anbarasan. Org. Lett. 2014, 16, 848-851.
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7. (a) G. Yan, A. Jyoti Borah and L. Wang. Org. Biomol. Chem.,
014, 12, 9557–9561; (b) M. Zhang, S. Zhang, C. Pan, and F.
H NMR (400 MHz, CDCl ): δ 8.20 (s, 1H), 7.57 (d, J =
3
2
8
7
6
(
1
1
.0Hz, 1H), 7.28 (d, J = 8.0 Hz, 1H), 7.25-7.19 (m, 3H), 7.15-
.11 (m, 1H), 7.08 (d, J = 8.0 Hz, 2H), 7.04 (d, J = 8.0 Hz, 2H),
.96 (d, J = 8.0 Hz, 2H), 2.32 (s, 3H), 2.25 (s, 3H). C NMR
101 MHz, CDCl ): δ 137.94, 136.86, 135.02, 134.80, 134.59,
30.94, 130.35, 130.26, 130.18, 129.62, 127.06, 123.60, 121.20,
19.84, 111.05, 108.41, 21.22, 21.05.
Chen. Synth. Commun., 2014: 19, 2844-2853; (c) S. Zhang, P.
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13
8
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(a) Q. Wu, D. Zhao, X. Qin, J. Lan and J. You. Chem. Commun.,
3
2
011, 47, 9188–9190. (b) Wang, S. Guo, R. Zhang, S. Lin and Z.
Yan. RSC Adv., 2016, 6, 54377; (c) Z. Xu, G. Lu, C. Cai. Org.
Biomol. Chem., 2017, 15, 2804–2808.
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9. (a) K. Yan, D. Yang, P. Sun, W. Wei, Y. Liu, G. Li, S.Lu, H.
Wang. Tetrahedron Lett, 2015, 56, 4792–4795; (b) S. K. R.
Parumala and R. K. Peddinti. Green Chem., 2015, 17, 4068–4072;
4
.28. 2-methyl-3-(p-tolylthio)-1H-indole[3ta]
1
H NMR (400 MHz, CDCl ): δ 8.14 (s, 1H), 7.54 (d, J = 7.8
Hz, 1H), 7.31 (d, J = 8.0 Hz, 1H), 7.17 (td, J = 8.0, 7.6, 1.2 Hz,
3
(c) Z. Huang, D. Zhang, X. Qi, Z. Yan, M. Wang, H. Yan, and A.
Lei. Org. Lett., 2016, 18 (10), 2351–2354.
1
H), 7.13-7.08 (m, 1H), 6.95 (s, 4H), 2.49 (s, 3H), 2.23 (s, 3H).
10. M. Raghavender Reddy, G. Santosh Kumar, H. M. Meshram.
Tetrahedron Lett, 2016, 57, 3622–3624.
13
C NMR (101 MHz, CDCl ) δ 141.03, 135.79, 135.52, 134.42,
3
1
1. (a) G. Rong, J. Mao, H. Yan, Y. Zheng and G. Zhang, J. Org.
Chem., 2015, 80, 4697–4703; (b) M. Zhang, P. Xie, W. Zhao, B.
Niu, W. Wu, Z. Bian, C. U. Pittman and A. Zhou, J. Org. Chem.,
1
2
30.45, 129.59, 125.88, 122.23, 120.76, 119.13, 110.71, 100.00,
0.97, 12.28.
[
22]
2
015, 80, 4176–4183; (c) W. Yu, P. Hu, Y. Fan, C. Yu, X. Yan,
4
.29. 1,2-Di-p-tolyldisulfane [4a]
X. Li and X. Xu, Org. Biomol. Chem., 2015, 13, 3308-3313; (d)
K. Xu, V. Khakyzadeh, T. Bury and B. Breit, J. Am. Chem. Soc.,
1
H NMR (400 MHz, CDCl ): δ 7.38 (d, J = 8.0 Hz, 4H), 7.10
3
2
014, 136, 16124–16127; (e) J. Zhang, Y. Shao, H. Wang, Q. Luo,
(d, J = 8.0 Hz, 4H), 2.32 (s, 6H).
J. Chen, D. Xu and X. Wan, Org. Lett., 2014, 16, 3312–3315; (f)
S. Guo, W. He, J. Xiang and Y. Yuan, Chem. Commun., 2014, 50,
[23]
4
.30. S-(p-Tolyl) 4-methylbenzenesulfonothioate [4b]
8
578–8581; (g) F.-L. Yang, F.-X. Wang, T.-T. Wang, Y.-J. Wang
1
and S.-K. Tian, Chem. Commun., 2014, 50, 2111–2113; (h) R.
Singh, D. S. Raghuvanshi and K. N. Singh, Org. Lett., 2013, 15,
H NMR (400 MHz, CDCl ): δ 7.46 (d, J = 8.4 Hz, 2H), 7.24
3
(
d, J = 8.4 Hz, 2H), 7.21 (d, J = 8.0 Hz, 2H), 7.14 (d, J = 8.0 Hz,
H), 2.42 (s, 3H), 2.38 (s, 3H). C NMR (101 MHz, CDCl ): δ
44.71, 142.17, 136.62, 130.33, 129.49, 127.73, 124.72, 21.80,
1.62.
4
202–4205; (i) X. Li, X. Xu, P. Hu, X. Xiao and C. Zhou, J. Org.
13
2
1
2
3
Chem., 2013, 78, 7343–7348; (j) X. Li, Y. Xu, W. Wu, C. Jiang,
C. Qi, and H. Jiang. Chem. Eur. J. 2014, 20, 1–6.
1
2. (a) X. Kang, R. Yan, G. Yu, X. Pang, X. Liu, X. Li, L. Xiang, and
G. Huang. J. Org. Chem., 2014, 79 (21), 10605–10610; (b) X.
Zhao, T. Li, L. Zhanga and K. Lu. Org. Biomol. Chem., 2016, 14,
4
2.43] 1. S-(4-Methoxyphenyl) 4-methylbenzenesulfonothioate [4e]
[
1
131–1137.
3. D. J. Ramón, G. Guillena, and X. Marset, Chem. Eur. J., 2017, 23,
0522–10526.
1
1
1
1
1
H NMR (400 MHz, CDCl ): δ 7.46 (d, J = 8.4 Hz, 2H), 7.27
3
4. P. Wang, S. Tang, P. F. Huang, and A. W. Lei, Angew. Chem. Int.
Ed., 2017, 56, 1–6.
5. P. Franzmanna, S. B. Beila, P. M. Winterscheidc, D.
Schollmeyera, S. R. Waldvogel, Synlett 2017; 28(08): 957–961.
(
2
d, J = 8.4 Hz, 2H), 7.22 (d, J = 8.0 Hz, 2H), 6.84 (d, J = 9.2 Hz,
H), 3.83 (s, 3H), 2.42 (s, 3H).
Acknowledgments
16. J. A. Fernández-Salas, A. P. Pulis, and D. J. Procter, Chem.
Commun., 2016, 52, 12364–12367.
1
7. F. Bottino, R. Fradullo, S. Pappalardo, J. Org. Chem., 1981, 46
13), 2793–2795.
8. P. Franzmanna, S. B. Beila, P. M. Winterscheidc, D.
We gratefully acknowledge financial support of this work by
the National Natural Science Foundation of China (No.
(
1
2
1563025), and the Program for Changjiang Scholars and
Schollmeyera, S. R. Waldvogel, Synlett., 2017, 28(08), 957-961.
Innovative Research Team in University (No. IRT_15R46), and
Yangtze River Scholar Research Project of Shihezi University
19. P. Anbarasan, H. Neumanna and M. Beller, Chem. Commun.,
011,47, 3233–3235.
2
2
2
2
2
0. H. L. Zhang, X. Z. Bao, Y. M. Song, J. P. Qu, B. M. Wang,
Tetrahedron, 2015, 71, 8885-8891.
1. F. X. Wang, S. D. Zhou, C. M. Wang and S. K. Tian, Org.
Biomol. Chem., 2017, 15, 5284-5288.
(No. CJXZ201601).
References and notes
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