Green Chemistry
Paper
Characterization data for representative products
12 P. G. Jessop, T. Ikariya and R. Noyori, Chem. Rev., 1999, 99,
475–494.
13 G. Musie, M. Wei, B. Subramaniam and D. H. Busch,
Coord. Chem. Rev., 2001, 219–221, 789–820.
14 J. P. Hallett, P. Pollet, C. L. Liotta and C. A. Eckert, Acc.
Chem. Res., 2008, 41, 458–467.
15 R. Scott Oakes, A. A. Clifford, K. D. Bartle, M. Thornton
Pett and C. M. Rayner, Chem. Commun., 1999, 247–248.
16 C. X. Miao, L. N. He, J. L. Wang and F. Wu, J. Org. Chem.,
2009, 75, 257–260.
17 A. H. Liu, R. Ma, M. Zhang and L. N. He, Catal. Today,
2012, 194, 38–43.
18 A. Yamaguchi, N. Hiyoshi, O. Sato, K. K. Bando and
M. Shirai, Green Chem., 2009, 11, 48–52.
19 M. McCarthy, H. Stemmer and W. Leitner, Green Chem.,
2002, 4, 501–504.
20 E. J. Beckman, J. Supercrit. Fluids, 2004, 28, 121–191.
21 J. P. Hallett, C. L. Kitchens, R. Hernandez, C. L. Liotta and
C. A. Eckert, Acc. Chem. Res., 2006, 39, 531–538.
22 H. Cheng, X. Meng, R. Liu, Y. Hao, Y. Yu, S. Cai and
F. Zhao, Green Chem., 2009, 11, 1227–1231.
23 J. L. Gohres, A. T. Marin, J. Lu, C. L. Liotta and C. A. Eckert,
Ind. Eng. Chem. Res., 2009, 48, 1302–1306.
Diphenyl sulfide.32 The product was obtained as a pale
1
yellow liquid. H NMR (400 MHz, CDCl3) δ: 7.39 (d, J = 7.4 Hz,
4 H), 7.34 (dd, J = 9.9, J = 4.8 Hz, 4 H), 7.28 (dd, J = 7.6, J =
5.1 Hz, 2 H). 13C NMR (100.6 MHz, CDCl3) δ: 135.86, 131.10,
129.25, 127.10. EI-MS, m/z (%): 186 (100) [M+].
Phenyl methyl sulfide.32 The product was obtained as a pale
yellow liquid. 1H NMR (400 MHz, CDCl3) δ: 7.32–7.20 (m, 4 H),
7.17–7.07 (m, 1 H), 2.47 (s, 3 H). 13C NMR (100.6 MHz, CDCl3)
δ: 138.40, 128.80, 126.61, 125.00, 15.83. EI-MS, m/z (%): 124
(100) [M+].
Pyridine.58 The product was obtained as a pale yellow
1
liquid. H NMR (400 MHz, CDCl3) δ: 8.67–8.55 (m, 2 H), 7.66
(dd, J = 10.7, J = 4.6 Hz, 1 H), 7.34–7.22 (m, 2 H). 13C NMR
(100.6 MHz, CDCl3) δ: 149.86, 135.93, 123.72. EI-MS, m/z (%):
88 (74) [M+].
4-Phenylpyridine.59 The product was obtained as a white
1
solid. H NMR (400 MHz, CDCl3) δ: 8.67 (d, J = 5.3 Hz, 2 H),
7.65 (d, J = 7.2 Hz, 2 H), 7.59–7.40 (m, 5 H). 13C NMR
(100.6 MHz, CDCl3) δ: 150.19, 148.47, 138.11, 129.13, 127.01,
121.67. EI-MS, m/z (%): 155 (100) [M+].
24 G. Li, H. Jiang and J. Li, Green Chem., 2001, 3, 250–251.
25 H. F. Jiang and X. Z. Huang, J. Supercrit. Fluids, 2007, 43,
291–294.
26 G. Gao, Y. Tao and J. Jiang, Green Chem., 2008, 10, 439–441.
27 H. F. Jiang and Y. S. Dong, Chin. J. Chem., 2008, 26,
1407–1410.
Acknowledgements
We are grateful to the National Natural Science Foundation of
China (Grant No. 21172125), the “111” Project of Ministry of
Education of China (Project No. B06005), and the Committee
of Science and Technology of Tianjin.
28 S. Liu, Y. Wang, J. Jiang and Z. Jin, Green Chem., 2009, 11,
1397–1400.
29 N. Hiyoshi, O. Sato, A. Yamaguchi and M. Shirai, Chem.
Commun., 2011, 47, 11546–11548.
30 K. C. Nicolaou, A. E. Koumbis, S. A. Snyder and
K. B. Simonsen, Angew. Chem., Int. Ed., 2000, 39,
2529–2533.
Notes and references
1 D. H. Gibson, Chem. Rev., 1996, 96, 2063–2096.
2 Z. Z. Yang, Y. N. Zhao and L. N. He, RSC Adv., 2011, 1,
545–567.
31 N. Iranpoor, H. Firouzabadi and H. R. Shaterian, J. Org.
Chem., 2002, 67, 2826–2830.
3 A. H. Liu, R. Ma, C. Song, Z. Z. Yang, A. Yu, Y. Cai,
L. N. He, Y. N. Zhao, B. Yu and Q. W. Song, Angew. Chem., 32 A. C. Fernandes, J. A. Fernandes, C. C. Romão, L. F. Veiros
Int. Ed., 2012, 51, 11306–11310. and M. J. Calhorda, Organometallics, 2010, 29, 5517–5525.
4 A. H. Liu, L. N. He, F. Hua, Z. Z. Yang, C. B. Huang, B. Yu 33 Y. Mikami, A. Noujima, T. Mitsudome, T. Mizugaki,
and B. Li, Adv. Synth. Catal., 2011, 353, 3187–3195.
5 Z. Z. Yang, L. N. He, Y. N. Zhao, B. Li and B. Yu, Energy
Environ. Sci., 2011, 4, 3971–3975.
6 Z. Z. Yang, L. N. He, J. Gao, A. H. Liu and B. Yu, Energy
Environ. Sci., 2012, 5, 6602–6639.
K. Jitsukawa and K. Kaneda, Chem.–Eur. J., 2011, 17,
1768–1772.
34 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, 321–327.
7 P. Markewitz, W. Kuckshinrichs, W. Leitner, J. Linssen, 35 Y. Wang and J. H. Espenson, Org. Lett., 2000, 2,
P. Zapp, R. Bongartz, A. Schreiber and T. E. Muller, Energy
Environ. Sci., 2012, 5, 7281–7305.
8 M. Chatterjee, H. Kawanami, M. Sato, T. Ishizaka,
T. Yokoyama and T. Suzuki, Green Chem., 2010, 12, 87–93.
9 M. Aresta and A. Dibenedetto, Dalton Trans., 2007,
2975–2992.
10 T. Sakakura, J. C. Choi and H. Yasuda, Chem. Rev., 2007,
107, 2365–2387.
11 H. Jiang, L. Jia and J. Li, Green Chem., 2000, 2, 161–164.
3525–3526.
36 S. Kumar, A. Saini and J. S. Sandhu, Tetrahedron Lett., 2005,
46, 8737–8739.
37 R. Sanz, J. Escribano, Y. Fernández, R. Aguado,
M. R. Pedrosa and F. J. Arnáiz, Synlett, 2005, 1389–1392.
38 B. W. Yoo, J. W. Choi and C. M. Yoon, Tetrahedron Lett.,
2006, 47, 125–126.
39 H. P. Kokatla, P. F. Thomson, S. Bae, V. R. Doddi and
M. K. Lakshman, J. Org. Chem., 2011, 76, 7842–7848.
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