RSC Advances
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RSC ADVANCES
DOI: 10.1039/C5RA01934F
Hz, 2H), 7.21ꢀ7.58 (m, 7H); EIꢀMS (70eV): m/z (%) = 200 (M+,
100).
5. Y. Chen, X. Shi, B. Han, H. Qin, Z. Li, Y. Lu, J. Wang, Y. Kong, J.
Nanosci. Nanotech. 2012, 12, 7239.
6. F. Torney, B. G. Trewyn, V. S. Y. Lin, K. Wang, Nature Nanotech.
Diphenylamine (Table 5, entry 1): White crystals, mp. 54ꢀ55 oC [34].
1H NMR (250 MHz, CDCl3):
δ
(ppm) 5.73 (s, br, 1H), 6.95 (t,
= 8.0Hz, 4H), 7.26ꢀ7.32 (m, 4H); EIꢀMS
(70eV): m/z (%) = 169 (M+, 100).
J =
2007,
7. M. Hajjami, F. Ghorbani, F. Bakhti, Appl. Catal. A. 2014, 470, 303.
8. R. M. MartinꢀAranda J. Cejka, Top Catal. 2010, 53,141.
2, 295.
7.2Hz, 2H), 7.10 (d,
J
,
9. L. Lv, K. Wang, X. S. Zhao, J. Colloid Interface Sci. 2007, 305, 218.
10. M. Yoshikazu, Y. Masanori, A. Eiichi, A. Sadao, T. Shunsuke, Ind.
Eng. Chem. Res. 2009, 48, 938.
4ꢀNitroꢀ
N
ꢀphenylaniline (Table 5, entry 6): yellow solid, mp. 134ꢀ
136 C [35]. 1H NMR (250 MHz, CDCl3):
(ppm) 6.50 (s, br, 1H),
= 9.0 Hz, 2H), 7.25ꢀ7.37 (m, 3H), 7.55 (t, = 7.2 Hz, 2H),
= 9.0 Hz, 2H); EIꢀMS (70eV): m/z (%) = 214 (M+, 100).
o
δ
6.94 (d,
8.19 (d,
J
J
J
11. I. I. Slowing, J. L. ViveroꢀEscoto, C. W. Wu, V. S. Y. Lin, Adv. Drug
Deliv. Rev. 2008, 60, 1278.
12. J. Y. Ying, C. P. Mehnert, M. S. Wong, Ang. Chem. Int. Ed. 1999, 38
,
4.4 General procedure for Stille-coupling of aryl halides with
Ph3SnCl catalyzed by MCM-41 dtz Pd(II)
56.
‐
‐
13. J. Demel, Sujandi, SꢀE. Park, J. Cejka, P. Stepnicka, J. Mol. Catal. A:
Chem. 2009, 302, 28.
Aryl halide (1.0 mmol) was added to a stirring mixture of
catalyst (5 mg) in PEGꢀ400. Then, Ph3SnCl (0.5 mmol) and K2CO3
(1.5 mmol) were added and stirred at room temperature. Monitoring
of the reaction with TLC analysis shown the reaction was completed
within 3 h. After the completion of the reaction, the catalyst was
separated by filtration and the reaction mixture was extracted with
H2O and EtOAc. The organic layer was dried over MgSO4 and then
evaporated under reduced pressure. The residue was purified by
14. J. Demel, M. Lamac, J. Cejka, P. Stepnicka, chem. Sus chem. 2009,
2
, 442.
15. B. Karimi, S. Abedi, J. H. Clark , V. Budarin, Angew.Chem., Int. Ed.
2006, 45, 4776.
16. M. Bakherad, A. Keivanloo, B. Bahramian, S. Jajarmi, J. Organomet.
Chem. 2013, 724, 206.
column chromatography on silica gel using nꢀhexane/EtOAc (7/3),
17. N. Iranpoor, H. Firouzabadi, E. EtemadiDavan, A. Rostami, A.
Nematollahi, J. Organomet. Chem. 2013, 740, 123.
afforded the desired products in good to excellent yields.Reaction
products were characterized by IR, H NMR and MS spectrometry.
1
Spectroscopy data for compounds 7 are in good agreement with
those previously reported.
18. H. J. Xu, Y. F. Liang, Z. Y. Cia, H. X. Qi, C. Y. Yang, Y. S. Feng, J.
Org. Chem. 2011, 76, 2296.
19. S. Varghese, C. Anand, D. Dhawale, A. Mano, V. V.
Balasubramanian, G. Allen Gnana Raj, S. Nagarajan, M. A. Wahab,
o
Biphenyl (Table 7, entries 1, 4 and 9): White solid, mp. 69 C [38].
1H NMR (250 MHz, CDCl3):
δ (ppm) 7.36ꢀ7.39 (m, 2H), 7.46ꢀ7.52
A. Vinu, Tetrahedron Letters. 2012, 53, 5656
20. L. Zhong, A. Chokkalingama, W. S. Chaa, K. S. Lakhia, X. Su, G.
Lawrence, A. Vinu, Catalysis Today. 2015, 243, 195.
(m, 4H), 7.64 (d,
100).
J
= 7.5Hz, 4H); EIꢀMS (70eV): m/z (%) = 154 (M+,
1
2ꢀMethylbiphenyl (Table 7, entry 6): Colourless oil [40]. H NMR
21. M. Semler, P. Stepnicka, Catalysis Today. 2015, 243, 128.
(250 MHz, CDCl3):
δ (ppm) 2.46 (s, 3H), 7.25ꢀ7.57 (m, 9H); MS
22. K. Köhler, R. G. Heidenreich, J. Pietsch, Chem. Eur. J. 2002, 8, 622.
(EI+): m/z: 168 (M +, 100).
23. D. E. Bergbreiter, P. L. Osburn, J. D. Frels, J. Am. Chem. Soc. 2001,
123, 11105.
Acknowledgements
24. J. M. Zhou, R. X. Zhou, L. Y. Mo, S. F. Zhao, X. M. Zheng, J. Mol.
Catal. 2002, 178, 289.
We are thankful to the University of Kurdistan Research Council
for partial support of this work.
25. M. Opanasenko, P. Stepnicka, J. Cejka, RSC Adv. 2014, 4, 65137.
26. M. Nikoorazm, A. GhorbaniꢀChoghamarani, F. Ghorbani, H.
Mahdavi, Z. Karamshahi, J. Porous. Mater. 2015, 22, 261.
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