Carboxylate-Based, Room-Temperature Ionic Liquids
[9] M. Brenda, A. Knebelkamp, A. Greiner, W. Heitz, Synlett
1991, 809–810.
[10] J. Hassan, V. Penalva, L. Lavenot, C. Gozzi, M. Lemaire, Tet-
rahedron 1998, 54, 13793–13804.
[11] S. Mukhopadhyay, G. Rothenberg, H. Wiener, Y. Sasson, Tet-
rahedron 1999, 55, 14763–14768.
[12] J. MO, J. Ruan, L. Xu, Z. Hyder, O. Saidi, S. Liu, W. Pei, J.
Xiao, J. Mol. Catal. A 2007, 261, 267–275.
[13] O. Mongin, L. Porres, L. Moreaux, J. Mertz, M. Blanchard-
Desce, Org. Lett. 2002, 4, 719–722.
[14] C. Glaser, Ber. Dtsch. Chem. Ges. 1869, 2, 422.
[15] a) S. M. Islam, P. Mondal, A. S. Roy, S. Mondal, D. Hossain,
Tetrahedron Lett. 2010, 51, 2067–2070; b) T. Fukuyama, M.
Shinmen, S. Nishitani, M. Sato, I. Ryu, Org. Lett. 2002, 4,
1691–1694.
was heated in an oil bath at 100 °C with stirring. The reaction was
followed by GC and TLC analyses. After completion of the reac-
tion (3.5 h), the mixture was cooled to room temperature and the
coupled product was extracted with diethyl ether (3ϫ3 mL). The
solvent was then evaporated and the residue was purified by
chromatography on a short column of silica gel using n-hexane/
ethyl acetate (5:1) as the eluent to give 1-methyl-4-(2-phenyleth-
ynyl)benzene in 92% yield. 1H NMR (250 MHz, CDCl3): δ = 7.46–
7.24 (m, 7 H), 7.17–7.06 (m, 2 H), 2.30 (s, 3 H) ppm. 13C NMR
(62.9 MHz, CDCl3): δ = 138.4, 132.5, 131.6, 129.1, 128.5, 128.3,
128.1, 123.5, 89.6, 88.7, 21.5 ppm.
Supporting Information (see footnote on the first page of this arti-
cle): Additional spectral data.
[16] a) T. Welton, Chem. Rev. 1999, 99, 2071–2084; b) P. Wasser-
scheid, W. Keim, Angew. Chem. 2000, 112, 3926–3945; Angew.
Chem. Int. Ed. 2000, 39, 3772–3789; c) J. Dupont, R. F. Souza,
P. A. Z. Suarez, Chem. Rev. 2002, 102, 3667–3692; d) J. S.
Wilkes, Green Chem. 2002, 4, 73–80.
[17] a) V. I. Parvulescu, C. Hardacre, Chem. Rev. 2007, 107, 2615–
2665; b) J. Durand, E. Teuma, M. Gomez, C. R. Chim. 2007,
10, 152–177; c) S. G. Zlotin, N. N. Makhova, Russ. Chem. Rev.
2010, 79, 543–583; d) Ionic Liquids in Synthesis (Eds.: P. Was-
serscheid, T. Welton), Wiley-VCH, Weinheim, 2008, vol. 1 and
2.
Acknowledgments
We are thankful for the partial support of this work by the Shiraz
University Research Council.
[1] a) V. Penalva, J. Hassan, L. Lavenot, C. Gozzi, M. Lemaire,
Tetrahedron Lett. 1998, 39, 2559–2560; b) W. M. Seganish,
M. E. Mowery, S. Riggleman, P. DeShong, Tetrahedron 2005,
61, 2117–2121; c) H. S. He, C. Zhang, C. K. W. Ng, P. H. Toy,
[18] Y. Li, J. Zhang, W. Wang, Q. Miao, X. She, X. Pan, J. Org.
Chem. 2005, 70, 3285–3287.
Tetrahedron 2005, 61, 12053–12057; d) N. Ma, Z. Duan, Y. Wu, [19] M. T. Rahman, T. Fukuyama, I. Ryu, K. Suzuki, K. Yone-
J. Organomet. Chem. 2006, 691, 5697–5700.
[2] J. Hassan, M. Sevignon, C. Gozzi, E. Schulz, M. Lemaire,
Chem. Rev. 2002, 102, 1359–1470.
[3] a) P. E. Fanta, Chem. Rev. 1964, 64, 613–632; b) P. E. Fanta,
Synthesis 1974, 9–21.
[4] M. Tieco, L. Testaferri, M. Tingoli, D. Chianelli, M. Montan-
ucci, Synthesis 1984, 736–738.
[5] A. Yanagisawa, H. Hibino, S. Habaue, Y. Hisada, H. Yamam-
oto, J. Org. Chem. 1992, 57, 6386–6387.
mura, P. F. Hughes, K. Nokihara, Tetrahedron Lett. 2006, 47,
2703–2706.
[20] P. G. Lima, O. A. C. Antunes, Tetrahedron Lett. 2008, 49,
2506–2509.
[21] A. R. Gholap, K. Venkatesan, R. Pasricha, T. Daniel, R. J. La-
hoti, K. V. Srinivasan, J. Org. Chem. 2005, 70, 4869–4872.
[22] S. B. Park, H. Alper, Tetrahedron Lett. 2004, 45, 5515–5517.
[23] N. Iranpoor, H. Firouzabadi, A. Azadi, J. Organomet. Chem.
2008, 693, 2469–2472.
[6] B. C. Rann, P. Dutta, A. Sarkar, Tetrahedron Lett. 1998, 39, [24] a) N. Iranpoor, H. Firouzabadi, A. Azadi, J. Organomet. Chem.
9557–9558.
2010, 695, 887–890; b) N. Iranpoor, H. Firouzabadi, R. Azadi,
Eur. J. Org. Chem. 2007, 2197–2201.
[25] N. Bicak, J. Mol. Liq. 2005, 116, 15–18.
[7] K. Abiraj, G. R. Srinivasa, D. C. Gowda, Tetrahedron Lett.
2004, 45, 2081–2084.
[8] C. Qi, X. Sun, C. Lu, J. Yang, Y. Du, H. Wu, X. M. Zhang, J.
Organomet. Chem. 2009, 694, 2912–2916.
Received: May 19, 2011
Published Online: November 17, 2011
Eur. J. Org. Chem. 2012, 305–311
© 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.eurjoc.org
311