Copyright (c) 2013 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Non-Acidic Mediated Friedel-Craft Reaction of Thiophene Using EtAlCl2
Corresponding Author(s) : Adnan Bulut
Asian Journal of Chemistry,
Vol. 25 No. 15 (2013): Vol 25 Issue 15
Abstract
Since alkyl Lewis acids are Brønsted bases, they give a non-acidic reaction media. In this context, acylation of thiophene is investigated in the presence of EtAlCl2 and non-acidic media. Besides 8 examples of thiophene, one example for pyrrole is synthesized in moderate to high yields (up to 99 %).
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- D.E. Pearson and C.A. Buehler, Synthesis, 533 (1972).
- A. Cihaner, O. Mert and A.S. Demir, Electrochim. Acta, 54, 1333 (2009).
- L.F. Schweiger, K.S. Ryder, D.G. Morris, A. Glidle and J.M. Cooper, J. Mater. Chem., 10, 107 (2000).
- A.I. El-Khawaga, M.F. El-Zohry and M.T. Ismail, Phosphorus Sulfur Silicon, 33, 25 (1987).
- R. Parella, N. Amitkumar and S.A. Babu, Tetrahedron Lett., 54, 1738 (2013).
- F. Richard, H. Carreyre and G. Perot, J. Catal., 159, 427(1996).
- H. Matsubara, S. Yasuda and I. Ryu, Synlett, 2, 247 (2003).
- V.I. Smirnov, A.V. Afanas’ev and L.I. Belen’kii, Chem. Heterocycl. Comp., 46, 1199 (2011).
- B.B. Snider, D.J. Rodini, M. Karras, T.C. Kirk, E.A. Deutsch, R. Cordova and R.T. Price, Tetrahedron, 37, 3927 (1981).
- B.B. Snider and A.C. Jackson, J. Org. Chem., 47, 5393 (1982).
- Ö. Dogan, V. Senol, S. Zeytinci, H. Koyuncu and A. Bulut, J. Organomet. Chem., 690, 430 (2005).
- M. Cai, G. Zheng and G. Ding, Green Chem., 11, 1687 (2009).
- M. Jaspars, B.J. Morrison and O.C. Musgrave, Tetrahedron, 59, 4153 (2003).
- J.-Y. Chen, S.-J. Chen, Y.-J. Tang, C.-Y. Mou and F.-Y. Tsai, J. Mol. Catal. A, 307, 88 (2009).
- F. Manjolinho, M.F. Grünberg, N. Rodriguez and L.J. Gooßen, Eur. J. Org. Chem., 25, 4680 (2012).
- J.H. Billmann and F.H. Travis, Proc.-Indian Acad. Sci. Chem. Sci., 54, 101 (1944).
- H. Li, M. Yang, Y. Qi and J. Xue, Eur. J. Org. Chem., 14, 2662 (2011).
- A.B. Zaitsev, E.Y. Schmidt,A.M. Vasil’tsov, A.I. Mikhaleva, O.V. Petrova, A.V. Afonin and N.V. Zorina, Chem. Heterocycl. Comp., 42, 34 (2006).
- T.D. Turbitt and W.E. Watts, J. Organomet. Chem., 46, 109(1972).
- T.H. Barr and W.E. Watts, Tetrahedron, 24, 3219 (1968).
- E. Yildiz, P. Camurlu, C. Tanyeli, I. Akhmedov and L. Toppare, J. Electroanal. Chem., 612, 247 (2008).
- A.B. Merrill and E. Legoff, J. Org. Chem., 55, 2904 (1990).
- W.Y. Leung and E. Legoff, Synth. Commun., 19, 787 (1989).
- J. Kagan and S.K. Arora, Heterocycles, 20, 1937 (1983).
- A. Merz and F. Ellenger, Synthesis, 462 (1991).
References
D.E. Pearson and C.A. Buehler, Synthesis, 533 (1972).
A. Cihaner, O. Mert and A.S. Demir, Electrochim. Acta, 54, 1333 (2009).
L.F. Schweiger, K.S. Ryder, D.G. Morris, A. Glidle and J.M. Cooper, J. Mater. Chem., 10, 107 (2000).
A.I. El-Khawaga, M.F. El-Zohry and M.T. Ismail, Phosphorus Sulfur Silicon, 33, 25 (1987).
R. Parella, N. Amitkumar and S.A. Babu, Tetrahedron Lett., 54, 1738 (2013).
F. Richard, H. Carreyre and G. Perot, J. Catal., 159, 427(1996).
H. Matsubara, S. Yasuda and I. Ryu, Synlett, 2, 247 (2003).
V.I. Smirnov, A.V. Afanas’ev and L.I. Belen’kii, Chem. Heterocycl. Comp., 46, 1199 (2011).
B.B. Snider, D.J. Rodini, M. Karras, T.C. Kirk, E.A. Deutsch, R. Cordova and R.T. Price, Tetrahedron, 37, 3927 (1981).
B.B. Snider and A.C. Jackson, J. Org. Chem., 47, 5393 (1982).
Ö. Dogan, V. Senol, S. Zeytinci, H. Koyuncu and A. Bulut, J. Organomet. Chem., 690, 430 (2005).
M. Cai, G. Zheng and G. Ding, Green Chem., 11, 1687 (2009).
M. Jaspars, B.J. Morrison and O.C. Musgrave, Tetrahedron, 59, 4153 (2003).
J.-Y. Chen, S.-J. Chen, Y.-J. Tang, C.-Y. Mou and F.-Y. Tsai, J. Mol. Catal. A, 307, 88 (2009).
F. Manjolinho, M.F. Grünberg, N. Rodriguez and L.J. Gooßen, Eur. J. Org. Chem., 25, 4680 (2012).
J.H. Billmann and F.H. Travis, Proc.-Indian Acad. Sci. Chem. Sci., 54, 101 (1944).
H. Li, M. Yang, Y. Qi and J. Xue, Eur. J. Org. Chem., 14, 2662 (2011).
A.B. Zaitsev, E.Y. Schmidt,A.M. Vasil’tsov, A.I. Mikhaleva, O.V. Petrova, A.V. Afonin and N.V. Zorina, Chem. Heterocycl. Comp., 42, 34 (2006).
T.D. Turbitt and W.E. Watts, J. Organomet. Chem., 46, 109(1972).
T.H. Barr and W.E. Watts, Tetrahedron, 24, 3219 (1968).
E. Yildiz, P. Camurlu, C. Tanyeli, I. Akhmedov and L. Toppare, J. Electroanal. Chem., 612, 247 (2008).
A.B. Merrill and E. Legoff, J. Org. Chem., 55, 2904 (1990).
W.Y. Leung and E. Legoff, Synth. Commun., 19, 787 (1989).
J. Kagan and S.K. Arora, Heterocycles, 20, 1937 (1983).
A. Merz and F. Ellenger, Synthesis, 462 (1991).