34
A. Kumbhar et al. / Journal of Organometallic Chemistry 738 (2013) 29e34
4.2. Typical procedure for preparation of desilicated ZSM-5 (2)
Acknowledgments
In a typical experiment, ZSM-5 (1.0 g) was treated with 0.20 M
Na2CO3 solution (about 30 mL/g) for 3 h at 75 ꢁC. After the first 3 h
period followed by washing with deionized water for 1 h at 75 ꢁC,
the sample was filtered and then submitted to another 3 h of
treatment with a fresh Na2CO3 solution of the same concentration.
The solid was filtered and washed several times with distilled
water. The desilicated zeolite was washed at 80 ꢁC with stirring in
distilled water (3 ꢂ 30 mL) to complete remove sodium silicate
from the medium, and finally, dried at 120 ꢁC, which yielded 0.80 g
white powder (2).
Financial support provided by the Department of Science and
Technology and the University Grants Commission, New Delhi,
India is warmly acknowledged with thanks. One of the authors
Arjun Kumbhar thanks UGC, New Delhi, India for the award of
Teacher Fellowship under the F.I.P. of the XIth Plan.
References
[1] S. Budavari, M.J. O’Neil, A. Smith, The Merk Index: An Encyclopedia of
Chemicals, Drugs and Biologicals, twelfth ed., Merk & Co, USA, 1996.
[2] J. Boren, M. Cascante, S. Marin, B. Comin-Anduix, J.J. Centelles, S. Lim,
S. Bassilian, S. Ahmed, W.N. Lee, L.G. Boros, J. Biol. Chem. 276 (2001) 37747e
37753.
4.3. Immobilization of Pd(OAc)2 onto desilicated ZSM-5 (3)
[3] R. Capdeville, E. Buchdunger, J. Zimmerman, A. Matter, Nat. Rev. Drug Discov.
1 (2002) 493e502.
[4] F.C. Krebs, M. Jørgensen, Macromolecules 35 (2002) 7200e7206.
[5] S. Lee, W. Lee, J. Cho, S. Park, J. Park, W. Shin, J. Lee, I. Kang, S. Moon, Mac-
romolecules 44 (2011) 5994e6001.
[6] N. Miyaura, T. Yanagi, A. Suzuki, Synth. Commun. 11 (1981) 513e519.
[7] S. Kotha, K. Lahiri, D. Kashinath, Tetrahedron 58 (2002) 9633e9695.
[8] A. de Meijere, F. Diederich, Metal-catalyzed Cross-coupling Reactions, second
ed., Wiley-VCH, Weinheim, 2004.
[9] N. Miyaura, A. Suzuki, Chem. Rev. 95 (1995) 2457e2483.
[10] L. Liu, Y. Zhang, Y. Wang, J. Org. Chem. 70 (2005) 6122e6125.
[11] A. Zotto, F. Amoroso, W. Baratta, P. Rigo, Eur. J. Org. Chem. (2009)
110e116.
In a 50 mL Schlenk tube containing a desilicated ZSM-5 (1.0 g) in
dry THF (20 mL) was added dropwise solution of Pd(OAc)2 (0.022g,
0.01 mol) at room temperature. The mixture was stirred for 48 h at
room temperature, the solvent was removed by evaporation and
the resultant solid was washed with diethyl ether (3 ꢂ 5 mL). Then
the obtained zeolite was allowed to dry at room temperature to
afford 0.90 g of Pd@desilicated ZSM-5 (3).
4.4. Typical experimental procedure for the SuzukieMiyaura
reaction
[12] A. Silva, J. Senra, L. Aguiar, A. Simas, A. de Souza, L. Malta, O. Antunes, Tet-
rahedron Lett. 51 (2010) 3883e3885.
In a typical procedure 50 mL Schlenk tube containing magnetic
stirring bar and equipped with reflux condenser was charged aryl
bromide (1.0 mmol), arylboronic acid (1.2 mmol), K2CO3 (2.0 mmol),
and 0.009 g catalyst (0.02 mol%) in ethanol (5 mL). The reaction
mixture was vigorously stirred at 80 ꢁC. After completion of the
reaction as monitored by TLC, the catalyst was separated out by
filtration, followed by washing with water and diethyl ether. The
filtrate was extracted with diethyl ether (3 ꢂ 10 mL). The combined
organic layers were collected, dried over anhydrous Na2SO4 and
concentrated in vacuum to afford crude product, which was puri-
fied by silica gel column chromatography (n-hexane:EtOAc ¼ 9:1).
[13] M. Perez-Lorenzo, J. Phys. Chem. Lett. 3 (2012) 167e174.
[14] A. Molnar, Chem. Rev. 111 (2011) 2251e2320.
[15] Y. Wang, D.R. Sauer, Org. Lett. 6 (2004) 2793e2796.
[16] B. Karimi, P.F. Akhavan, Chem. Commun. (2009) 3750e3752.
[17] G. Durgun, O. Aksın, L. Artok, J. Mol. Catal. A: Chem. 278 (2007)
189e195.
[18] H. Bulut, L. Artok, S. Yilmaz, Tetrahedron Lett. 44 (2003) 289e291.
[19] L. Artok, H. Bulut, Tetrahedron Lett. 45 (2004) 3881e3884.
[20] M. Choi, D.-H. Lee, K. Na, B.-W. Yu, R. Ryoo, Angew. Chem. 121 (2009) 3727e
3730.
[21] L. Djakovitch, K. Koehler, J. Am. Chem. Soc. 123 (2001) 5990e5999.
[22] D.S. Bhange, V. Ramaswamy, Microporous Mesoporous Mater. 130 (2010)
322e326.
[23] D.S. Bhange, V. Ramaswamy, Microporous Mesoporous Mater. 103 (2007)
235e242.
[24] C.M.A. Parlett, K. Wilson, A.F. Lee, Chem. Soc. Rev. 42 (2013) 3876e3893.
[25] M. Choi, K. Na, J. Kim, Y. Sakamoto, O. Terasaki, R. Ryoo, Nature 461 (2009)
246e250.
[26] Y. Nishina, K. Takami, Green Chem. 14 (2012) 2380e2383.
[27] A. Kumbhar, S. Kamble, S. Jadhav, G. Rashinkar, R. Salunkhe, Tetrahedron Lett.
54 (2013) 1331e1337.
[28] P.S.E. Dai, D.E. Sherwood Jr., B.R. Martin, US5069890, 1991.
[29] J. Perez-Ramirez, C.H. Christensen, K. Egeblad, C.H. Christensen, J.C. Groen,
Chem. Soc. Rev. 37 (2008) 2530e2542.
[30] Y. Tao, H. Kanoh, L. Abrams, K. Kaneko, Chem. Rev. 106 (2006) 896e910.
[31] M. Ogura, S.Y. Shinomiya, J. Tateno, Y. Nara, M. Nomura, E. Kikuchi,
M. Matsukata, Appl. Catal. A 219 (2001) 33e43.
4.5. Spectral data of representative compounds
4.5.1. 4-phenyl benzophenone (Table 4, entry 7)
White solid, mp 99e100 ꢁC; 1H NMR (300 MHz, CDCl3,
d ppm):
7.35e7.40 (m, 1H), 7.46e7.54 (m, 4H), 7.58 (d, 1H, J ¼ 1.5 Hz), 7.60e
7.64 (m, 2H), 7.71 (d, 2H, J ¼ 8.4 Hz), 7.83 (d, 2H, J ¼ 8.4 Hz), 7.92 (d,
2H, J ¼ 8.4 Hz); 13C NMR (75 MHz, CDCl3,
d ppm): 126.6, 127.0, 128.1,
128.2, 128.8, 129.9, 130.4, 131.9, 136.0, 137.9, 140.1, 144.9, 196.0; MS
(ESI): m/z 258.
[32] L. Su, L. Liu, J. Zhuang, H. Wang, Y. Li, W. Shen, Y. Xu, X. Bao, Catal. Lett. 91
(2003) 155e167.
4.5.2. 2,4,6-trimethylbiphenyl (Table 4, entry 8)
[33] J.C. Groen, J.A. Moulijn, J. Perez-Ramirez, J. Mater. Chem. 16 (2006) 2121e
2131.
[34] M. Bjorgen, F. Joensen, M.S. Holm, U. Olsbye, K.-P. Lillerud, S. Svelle, Appl.
Catal. A: Gen. 345 (2008) 43e50.
[35] M.T. Reetza, J.G. de Vries, Chem. Commun. (2004) 1559e1563.
[36] J.A. Gladysz, Pure Appl. Chem. 73 (2001) 1319e1324.
Colorless liquid; 1H NMR (300 MHz, CDCl3,
d
ppm): 2.27 (s, 3H),
2.43 (s, 6H), 6.92 (d, 2H, J ¼ 2.5 Hz), 7.15e7.17 (m, 1H), 7.34e7.48 (m,
4H); 13C NMR (75 MHz, CDCl3,
ppm): 20.6, 23.9,127.0,128.0,128.4,
128.6, 129.0, 129.3, 135.6, 136.0, 136.3, 137.9; MS (ESI): m/z 196.
d