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A Simple and Efficient Iodination of Aromatic Compounds Using I2/Choline Chloride/K2S2O8
Corresponding Author(s) : R. Joel Karunakaran
Asian Journal of Chemistry,
Vol. 30 No. 7 (2018): Vol 30 Issue 7
Abstract
A simple and efficient method for the iodination of aromatic compounds has been achieved in the presence of molecular iodine, choline chloride and potassium peroxodisulfate at 65 °C in acetonitrile. The rate of conversion of aromatic compounds into iodoaromatic compounds was promoted by in situ formed choline peroxodisulfate. This protocol provides an efficient access to iodoarenes with operational simplicity, good functional group tolerance and a moderate to good product yield
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- A. Butler and J.V. Walker, Chem. Rev., 93, 1937 (1993); https://doi.org/10.1021/cr00021a014.
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- D.-W. Gao, Q. Gu and S.-L. You, ACS Catal., 4, 2741 (2014); https://doi.org/10.1021/cs500813z.
- C. Lu, S.-Y. Zhang, G. He, W.A. Nack and G. Chen, Tetrahedron, 70, 4197 (2014); https://doi.org/10.1016/j.tet.2014.02.070.
- A. Bose and P. Mal, Tetrahedron Lett., 55, 2154 (2014); https://doi.org/10.1016/j.tetlet.2014.02.064.
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- R. Badri and M. Gorjizadeh, Chem. Lett., 20, 1439 (2009); https://doi.org/10.1016/j.cclet.2009.06.017.
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- S.G. Yang and Y.H. Kim, Tetrahedron Lett., 40, 6051 (1999); https://doi.org/10.1016/S0040-4039(99)01236-8.
- H. Adibi, J. Chem. Res., 294 (2004); https://doi.org/10.3184/0308234041209202.
- R. Abdol, OPPI BRIEFS, 37, 279 (2005).
- N.C. Ganguly, S.K. Barik and S. Dutta, Synthesis, 1467 (2010); https://doi.org/10.1055/s-0029-1218698.
- R. Sathiyapriya and R.J. Karunakaran, Synth. Commun., 36, 1915 (2006); https://doi.org/10.1080/00397910600602750.
- R.J. Karunakaran and R. Sathiyapriya, Asian J. Chem., 18, 1321 (2006).
- R. Sathiyapriya and R.J. Karunakaran, E-J. Chem., 3, 65 (2006); https://doi.org/10.1155/2006/367389.
- R.J. Karunakaran and R. Sathiyapriya, J. Chem. Res., 575 (2006); https://doi.org/10.3184/030823406778521383.
- J. Iskra, S. Stavber and M. Zupan, Synthesis, 1869 (2004); https://doi.org/10.1055/s-2004-829136.
- B.L. Gadilohar, H.S. Kumbhar and G.S. Shankarling, Ind. Eng. Chem. Res., 53, 19010 (2014); https://doi.org/10.1021/ie5032919.
References
A. Butler and J.V. Walker, Chem. Rev., 93, 1937 (1993); https://doi.org/10.1021/cr00021a014.
P.B.D. de la Mare, Electrophilic Halogenation: Reaction Pathways Involving Attack by Electrophilic Halogens on Unsaturated Compounds, Cambridge University Press, New York (1976).
H.H. Hodgson, Chem. Rev., 40, 251 (1947); https://doi.org/10.1021/cr60126a003.
V. Snieckus, Chem. Rev., 90, 879 (1990); https://doi.org/10.1021/cr00104a001.
F. Diederich and P.J. Stang, Metal-Catalyzed Cross-Coupling Reactions, Wiley-VCH, New York (1997).
X. Zhao, F. Ding, J. Li, K. Lu, X. Lu, B. Wang and P. Yu, Tetrahedron Lett., 56, 511 (2015); https://doi.org/10.1016/j.tetlet.2014.12.029.
M.-L. Yao, G.W. Kabalka, D.W. Blevins, M.S. Reddy and L. Yong, Tetrahedron, 68, 3738 (2012); https://doi.org/10.1016/j.tet.2012.03.016.
F. Tramutola, L. Chiummiento, M. Funicello and P. Lupattelli, Tetrahedron Lett., 56, 1122 (2015); https://doi.org/10.1016/j.tetlet.2015.01.040.
A. Vibhute, S. Mokle, K. Karamunge, V. Gurav and Y. Vibhute, Chin. Chem. Lett., 21, 914 (2010); https://doi.org/10.1016/j.cclet.2010.04.008.
S. Wan, S.R. Wang and W. Lu, J. Org. Chem., 71, 4349 (2006); https://doi.org/10.1021/jo060424x.
J.S. Yadav, G. Kondaji, M. Shiva Ram Reddy and P. Srihari, Tetrahedron Lett., 49, 3810 (2008); https://doi.org/10.1016/j.tetlet.2008.03.151.
C.-Y. Zhou, J. Li, S. Peddibhotla and D. Romo, Org. Lett., 12, 2104 (2010); https://doi.org/10.1021/ol100587j.
M.S. Yusubov, E.N. Tveryakova, E.A. Krasnokutskaya, I.A. Perederyna and V.V. Zhdankin, Synth. Commun., 37, 1259 (2007); https://doi.org/10.1080/00397910701216039.
A.-S. Castanet, F. Colobert and P.-E. Broutin, Tetrahedron Lett., 43, 5047 (2002); https://doi.org/10.1016/S0040-4039(02)01010-9.
D. Dolenc, Synlett, 544 (2000); https://doi.org/10.1055/s-2000-6561.
P. Zhang, D. Sun, M. Wen, J. Yang, K. Zhou and Z. Wang, Adv. Synth. Catal., 354, 720 (2012); https://doi.org/10.1002/adsc.201100765.
T. Yamamoto, K. Toyota and N. Morita, Tetrahedron Lett., 51, 1364 (2010); https://doi.org/10.1016/j.tetlet.2009.12.125.
D.-W. Gao, Q. Gu and S.-L. You, ACS Catal., 4, 2741 (2014); https://doi.org/10.1021/cs500813z.
C. Lu, S.-Y. Zhang, G. He, W.A. Nack and G. Chen, Tetrahedron, 70, 4197 (2014); https://doi.org/10.1016/j.tet.2014.02.070.
A. Bose and P. Mal, Tetrahedron Lett., 55, 2154 (2014); https://doi.org/10.1016/j.tetlet.2014.02.064.
X.-C. Wang, Y. Hu, S. Bonacorsi, Y. Hong, R. Burrell and J.-Q. Yu, J. Am. Chem. Soc., 135, 10326 (2013); https://doi.org/10.1021/ja4055492.
D.A. House, Chem. Rev., 62, 185 (1962); https://doi.org/10.1021/cr60217a001.
J.M. Anderson and J.K. Kochi, J. Am. Chem. Soc., 92, 1651 (1970); https://doi.org/10.1021/ja00709a039.
R. Badri and M. Gorjizadeh, Chem. Lett., 20, 1439 (2009); https://doi.org/10.1016/j.cclet.2009.06.017.
H. Tajik, A.A. Esmaeili, I. Mohammadpoor-Baltork, A. Ershadi and H. Tajmehri, Synth. Commun., 33, 1319 (2003); https://doi.org/10.1081/SCC-120018691.
S.G. Yang and Y.H. Kim, Tetrahedron Lett., 40, 6051 (1999); https://doi.org/10.1016/S0040-4039(99)01236-8.
H. Adibi, J. Chem. Res., 294 (2004); https://doi.org/10.3184/0308234041209202.
R. Abdol, OPPI BRIEFS, 37, 279 (2005).
N.C. Ganguly, S.K. Barik and S. Dutta, Synthesis, 1467 (2010); https://doi.org/10.1055/s-0029-1218698.
R. Sathiyapriya and R.J. Karunakaran, Synth. Commun., 36, 1915 (2006); https://doi.org/10.1080/00397910600602750.
R.J. Karunakaran and R. Sathiyapriya, Asian J. Chem., 18, 1321 (2006).
R. Sathiyapriya and R.J. Karunakaran, E-J. Chem., 3, 65 (2006); https://doi.org/10.1155/2006/367389.
R.J. Karunakaran and R. Sathiyapriya, J. Chem. Res., 575 (2006); https://doi.org/10.3184/030823406778521383.
J. Iskra, S. Stavber and M. Zupan, Synthesis, 1869 (2004); https://doi.org/10.1055/s-2004-829136.
B.L. Gadilohar, H.S. Kumbhar and G.S. Shankarling, Ind. Eng. Chem. Res., 53, 19010 (2014); https://doi.org/10.1021/ie5032919.