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An Efficient Conversion of Alcohols to Alkyl Bromides Using Pyridinium Based Ionic Liquids: A Green Alternative to Appel Reaction
Corresponding Author(s) : Pranab J. Das
Asian Journal of Chemistry,
Vol. 30 No. 3 (2018): Vol 30 Issue 3
Abstract
Pyridinium based ionic liquids namely 4-alkylpyridinium bromides were prepared and used for the conversion of alcohols to alkyl bromides in the presence of p-toluenesulphonic acid in the absence of volatile organic compounds. This solvent free procedure promises to be a much improved and environmentally benign alternative to the Appel reaction.
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- J.R. Nohring, C.N. Hammond, C.N. Morrill and D.C. Neckers, Experimental Organic Chemistry, W.H. Freeman and Co., NY (1998).
- R. Appel, R. Kleinstueck and K.D. Ziehn, Angew Chem. Int. Ed. Engl. 10, 132 (1971); https://doi.org/10.1002/anie.197101321.
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- R. Ling, M. Yoshida and P.S. Mariano, J. Org. Chem., 61, 4439 (1996); https://doi.org/10.1021/jo960316i.
- E. Arstad, A.G.M. Barrett, B.T. Hopkins and J. Köbberling, Org. Lett., 4, 1975 (2002); https://doi.org/10.1021/ol026008q.
- R.M. Denton, J. An, B. Adeniran, A.J. Blake, W. Lewis and A.M. Poulton, J. Org. Chem., 76, 6749 (2011); https://doi.org/10.1021/jo201085r.
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- J.M.R. Narayanam, J.W. Tucker and C.R.J. Stephenson, J. Am. Chem. Soc., 131, 8756 (2009); https://doi.org/10.1021/ja9033582.
- N.E. Leadbeater, H.M. Torenius and H. Tye, Tetrahedron, 59, 2253 (2003); https://doi.org/10.1016/S0040-4020(03)00214-X.
- R.X. Ren and J.X. Wu, Org. Lett., 3, 3727 (2001); https://doi.org/10.1021/ol016672r.
- C.F. Petten, H.A. Kalviri and F.M. Kerton, Sustain. Chem. Process., 3, 16 (2015); https://doi.org/10.1186/s40508-015-0043-4.
- B.C. Ranu and R. Jana, Eur. J. Org. Chem., 755 (2005); https://doi.org/10.1002/ejoc.200400597.
- S. Crosignani, B. Nadal, Z. Li and B. Linclau, Chem. Commun., 21, 260 (2003); https://doi.org/10.1039/b211424k.
- S.G. Newman, C.S. Bryan, D. Perez and M. Lautens, Synthesis, 342 (2001); https://doi.org/10.1055/s-0030-1258368.
- P. Verdía, E.J. González, B. Rodríguez-Cabo and E. Tojo, Green Chem., 13, 2768 (2011); https://doi.org/10.1039/c1gc15408g.
- A. Aupoix, B. Pe’got and G. Vo-Thanh, Tetrahedron, 66, 1352 (2010); https://doi.org/10.1016/j.tet.2009.11.110
References
J.R. Nohring, C.N. Hammond, C.N. Morrill and D.C. Neckers, Experimental Organic Chemistry, W.H. Freeman and Co., NY (1998).
R. Appel, R. Kleinstueck and K.D. Ziehn, Angew Chem. Int. Ed. Engl. 10, 132 (1971); https://doi.org/10.1002/anie.197101321.
O. Mitsunobu, Synthesis, 1 (1981); https://doi.org/10.1055/s-1981-29317.
L. De Luca, G. Giacomelli and A. Porcheddu, Org. Lett., 4, 553 (2002); https://doi.org/10.1021/ol017168p.
R. Ling, M. Yoshida and P.S. Mariano, J. Org. Chem., 61, 4439 (1996); https://doi.org/10.1021/jo960316i.
E. Arstad, A.G.M. Barrett, B.T. Hopkins and J. Köbberling, Org. Lett., 4, 1975 (2002); https://doi.org/10.1021/ol026008q.
R.M. Denton, J. An, B. Adeniran, A.J. Blake, W. Lewis and A.M. Poulton, J. Org. Chem., 76, 6749 (2011); https://doi.org/10.1021/jo201085r.
L. Desmaris, N. Percina, L. Cottier and D. Sinou, Tetrahedron Lett., 44, 7589 (2003); https://doi.org/10.1016/j.tetlet.2003.08.064.
J.M.R. Narayanam, J.W. Tucker and C.R.J. Stephenson, J. Am. Chem. Soc., 131, 8756 (2009); https://doi.org/10.1021/ja9033582.
N.E. Leadbeater, H.M. Torenius and H. Tye, Tetrahedron, 59, 2253 (2003); https://doi.org/10.1016/S0040-4020(03)00214-X.
R.X. Ren and J.X. Wu, Org. Lett., 3, 3727 (2001); https://doi.org/10.1021/ol016672r.
C.F. Petten, H.A. Kalviri and F.M. Kerton, Sustain. Chem. Process., 3, 16 (2015); https://doi.org/10.1186/s40508-015-0043-4.
B.C. Ranu and R. Jana, Eur. J. Org. Chem., 755 (2005); https://doi.org/10.1002/ejoc.200400597.
S. Crosignani, B. Nadal, Z. Li and B. Linclau, Chem. Commun., 21, 260 (2003); https://doi.org/10.1039/b211424k.
S.G. Newman, C.S. Bryan, D. Perez and M. Lautens, Synthesis, 342 (2001); https://doi.org/10.1055/s-0030-1258368.
P. Verdía, E.J. González, B. Rodríguez-Cabo and E. Tojo, Green Chem., 13, 2768 (2011); https://doi.org/10.1039/c1gc15408g.
A. Aupoix, B. Pe’got and G. Vo-Thanh, Tetrahedron, 66, 1352 (2010); https://doi.org/10.1016/j.tet.2009.11.110