JOURNAL OF CHEMICAL RESEARCH 2013 21
2
6
Di(4-fluorophenyl) sulfide (2i), Table 2, entry 12: Colourless oil.
11 G. Li, Angew. Chem. Int. Ed., 2001, 40, 1513.
12 M. Murata and S.L. Buchwald, Tetrahedron, 2004, 60, 7397.
1
13
H NMR (400 MHz, CDCl /TMS): δ = 7.34–7.35 (m, 4H). C NMR
3
1
3
M.A. Fernández-Rodríguez, Q. Shen and J.F. Hartwig, Chem. Eur. J., 2006,
12, 7782.
(
1
CDCl , 100 MHz): δ = 163.3, 161.0, 133.2, 133.1, 131.4, 116.5,
3
+
16.5. MS (EI, m/z): 222 [M ].
26
1
1
4
5
T. Itoh and T. Mase, Org. Lett., 2004, 6, 4587.
Y. Zhang, K.N. Ngeow and J. Ying, Org. Lett., 2007, 9, 3495.
Di(3-fluorophenyl) sulfide (2j), Table 2, entry 13: Colourless oil.
1
13
H NMR (400 MHz, CDCl /TMS): δ = 7.23–7.41 (m, 4H). C NMR
3
16 S. Jammi, P. Barua, L. Rout, P. Saha and T. Punniyamurthy, Tetrahedron
Lett., 2008, 49, 1484.
17 Y. Wong, T.T. Jayanth and C. Cheng, Org. Lett., 2006, 8, 5613.
18 V.P. Reddy, K. Swapna, A.V. Kumar and K. Rao, J. Org. Chem., 2009, 74,
3189.
(
1
CDCl , 100 MHz): δ = 163.5, 161.3, 133.7, 133.4, 131.7, 116.9,
3
+
16.8. MS (EI, m/z): 222 [M ].
43
Di(2-dichlorophenyl) sulfide (2k), Table 2, entry 14: Colourless
oil. H NMR (400 MHz, CDCl /TMS): δ = 7.62 (d, J = 7.8 Hz, 2H),
.21 (t, J = 7.3 Hz, 2H), 7.12 (t, J = 7.5 Hz, 4H) C NMR (CDCl3,
00 MHz): δ =135.6, 133.2, 132.5, 128.7, 128.2, 125.6. MS (EI, m/z):
1
3
13
19 V.P. Reddy, A.V. Kumar, K. Swapna and K. Rao, Org. Lett., 2009, 11,
7
1
2
1
697.
+
20 S.N. Murthy, B. Madhav, V.P. Reddy, Y.V. Durga–Nageswar, Eur. J. Org.
Chem., 2009, 5902.
54, 256, 258 [M ].
Di(2-naphthyl) sulfide (2l), Table 2, entry 16: White solid. m.p.
2
1 A. Correa, M. Carril and C. Bolm, Angew. Chem. Int. Ed., 2008, 47, 2880.
44
1
1
58–160 °C (lit. 157–160 °C); H NMR (400 MHz, CDCl /TMS):
3
13
22 W. Wu, J. Wang and F.Y. Tsai, Green. Chem., 2009, 11, 326.
δ = 7.46–7.54 (m, 6H); 7.73–7.77 (m, 6H); 7.92 (br s, 2H). C NMR
100 MHz, CDCl /TMS): δ = 134.1, 132.6, 132.4, 129.9, 128.6, 128.0,
23 S.V. Ley and A.W. Thomas, Angew. Chem. Int. Ed., 2003, 42, 5400.
24 I.P. Beletskaya and A.V. Cheprakov, Coord. Chem. Rev., 2004, 248, 2337.
25 H. Firouzabadi, N. Iranpoor and M. Gholinejad, Adv. Synth. Catal., 2010,
(
1
3
26.8, 126.4, 125.9, 125.1. MS (EI, m/z): 286 [M+].
3
52, 119.
F. Ke, Y. Qu, Z. Jiang, Z. Li, D. Wu and X. Zhou, Org. Lett., 2011, 13,
54.
27 S. Zhang, P. Qian, M. Zhang, M. Hu and J. Cheng, J. Org. Chem., 2010, 75,
732.
D. Ma, S. Xie, P. Xue, X. Zhang, J. Dong, Y. Jiang, Angew. Chem. Int. Ed.,
009, 48, 4222.
W. You, X. Yan, Q. Liao and C. Xi, Org. Lett., 2010, 12, 3930.
2
6
This project was sponsored by the Jiangxi Provincial Natural
Science Foundation (project no. 2010GQH0064) and Jiangxi
Provincial Educational Commission Science and Technology
Planning Project (project no. GJJ11066), we also thank the
Analysis and Testing Centre of Jiangxi Normal University for
NMR measurements.
4
6
2
2
8
9
2
30 C. Lai and B.J. Backes, Tetrahedron Lett., 2007, 48, 3033.
3
3
1
2
N. Park, K. Park, M. Jang and S. Lee, J. Org. Chem., 2011, 76, 4371.
S. Narayan, J. Muldoon, M.G. Finn, V.V. Fokin, H.C. Kolb and
K.B. Sharpless, Angew. Chem., Int. Ed., 2005, 44, 3275.
C. Li, Chem. Rev., 2005, 105, 3095.
Received 12 July 2012; accepted 3 November 2012
Paper 1201277 doi: 10.3184/174751912X13545509224571
Published online: 15 January 2013
3
3
34 D. Dallinger and C.O. Kappe, Chem. Rev., 2007, 107, 2563.
3
3
3
5
6
7
A. Chanda and V.V. Fokin, Chem. Rev., 2009, 109, 725.
J. Chen, T. Yuan, W. Hao and M. Cai, Tetrahedron Lett., 2011, 52, 3710.
J. Chen, T. Yuan, W. Hao and M. Cai, Catal. Commun., 2011, 12, 1463.
References
1
D.N. Jones, Comprehensive organic chemistry, D.H. Barton and
D.W. Ollis, eds. Pergamon, New York, 1979, Vol. 3.
M.Tiecco, Synthesis, 1988, 749.
38 H. Hauptmann, W. Walter, C. Marino, J. Am. Chem. Soc., 1958, 80, 5832.
39 J.H. Clark, C.W. Jones, C.V.A. Duke and J.M. Miller, J. Chem. Soc. Chem.
Commun. 1989, 81.
40 V.N. Artem‘eva, P.I. Chupans, N.V. Kukarkina, G.N. Fedorova,
Y.N. Sazanov, V.M. Denisov and V.V. Kudryavtsev, Russ. J. Appl. Chem.,
2000, 73, 860.
41 N. García, P. García-García, M.A. Fernández-Rodríguez, R. Rubio,
M.R. Pedrosa, F.J. Arnáiz and R. Sanz, Adv. Synth. Catal., 2012, 354, 321.
42 X. Du, H. Liu and D. Du, Tetrahedron: Asymmetry, 2010, 21, 241.
43 G. Montaudo, P. Finocchiaro, E. Trivellone, F. Bottin and P. Maravigna,
Tetrahedron, 1971, 27, 2125.
44 K. Sadorn, W. Sinananwanich, J. Areephong, C. Nerungs, C. Wongma,
C. Pakawatchai and T. Thongpanchang, Tetrahedron Let., 2008, 49, 4519.
2
3
J. Hassan, M. Sevignon, C. Gozzi, E. Schulz and M. Lemaire, Chem. Rev.,
2
002, 102, 1359.
4
5
6
7
8
9
0
I.P. Beletskaya and A.V. Cheprakov, Coord. Chem. Rev., 2004, 248, 2337.
S.V. Ley and A.W. Thoma, Angew. Chem. Int. Ed., 2003, 42, 5400.
P.S. Herradura, K.A. Pendola and R.K. Guy, Org. Lett., 2000, 2, 2019.
D.J. Procter, J. Chem. Soc. Perkin Trans., 1 2001, 335.
J. Lindley, Tetrahedron, 1984, 40, 1433.
F.G. Bordwell and W.H. McKellin, J. Am. Chem. Soc., 1951, 73, 2251.
T. Migita, T. Shimisu, Y. Asami, J. Shiobara, Y. Kato and M. Kosugi, Bull.
Chem. Soc. Jpn., 1980, 53, 1385
1