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Ultrasonically Assisted Halogenation of Aromatic Compounds using Isoquinolinium Bound Hypervalent Chromium and Tetrabutylammonium Halides in PEG-600 Solutions under Acid Free and Solvent-Free Conditions
Asian Journal of Chemistry,
Vol. 30 No. 8 (2018): Vol 30 Issue 8
Abstract
Isoquinolinium bound Cr(VI) reagents like isoquinolinium dichromate (IQDC) and isoquinolinium chlorochromate (IQCC) have been successfully accomplished as efficient reagents for oxidative halogenation of aromatic compounds using tetrabutylammonium halide (TBAX) as halogenating agents in aqueous polyethylene glycol (PEG-600) under acid free conditions. Tetrabutylammonium bromide (TBAB) has been used for bromination and tetrabutylammonium iodide (TBAI) for iodination. The halogenation reactions that occurred smoothly in 2 to 7 h under conventional conditions are accelerated magnificently under sonication with few minutes (25 to 70 min) of reaction time and fairly good yields. The reactions occurred at moderate temperature under mild and environmentally safe conditions with simple work up.
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References
R.N. Boyd and R.T. Morrison, Organic Chemistry, Englewood Cliffs, Prentice Hall: New Jersey (1992).
U. Beck and E. Löser, Chlorinated Benzenes and Other NucleusChlorinated Aromatic Hydrocarbons, Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim (2012).
E.R. Atkinson, D.M. Murphy and J.E. Lufkin, Org. Synth., 4, 872 (1951).
V. Paul, A. Sudalai, T. Daniel and K.V. Srinivasan, Tetrahedron Lett., 35, 7055 (1994); https://doi.org/10.1016/0040-4039(94)88224-X.
J. Yousefi-Seyf, K. Tajeian, E. Kolvari, N. Koukabi, A. Khazaei and M.A. Zolfigol, Bull. Korean Chem. Soc., 33, 2619 (2012); https://doi.org/10.5012/bkcs.2012.33.8.2619.
Y. Liu and S. Zhou, Org. Lett., 7, 4609 (2005); https://doi.org/10.1021/ol051659i.
R. Johnsson, A. Meijer and U. Ellervik, Tetrahedron, 61, 11657 (2005); https://doi.org/10.1016/j.tet.2005.09.051.
T.I. Richardson, C.A. Clarke, K.L. Yu, Y.K. Yee, T.J. Bleisch, J.E. Lopez, S.A. Jones, N.E. Hughes, B.S. Muehl, C.W. Lugar, T.L. Moore, P.K. Shetler, R.W. Zink, J.J. Osborne, C. Montrose-Rafizadeh, N. Patel, A.G. Geiser, R.J.S. Galvin and J.A. Dodge, ACS Med. Chem. Lett., 2, 148 (2011); https://doi.org/10.1021/ml100220b.
T.A. Khan, S. Kumar, C. Venkatesh and H. Ila, Tetrahedron, 67, 2961 (2011); https://doi.org/10.1016/j.tet.2011.02.043.
S.N. Joshi, S.M. Vyas, H. Wu, M.W. Duffel, S. Parkin and H.J. Lehmler, Tetrahedron, 67, 7461 (2011); https://doi.org/10.1016/j.tet.2011.07.064.
B. Kuotsu, E. Tiewsoh, A. Debroy and M.K. Mahanti, J. Org. Chem., 61, 8875 (1996); https://doi.org/10.1021/jo961079m.
A. Suzuki, Pure Appl. Chem., 63, 419 (1991); https://doi.org/10.1351/pac199163030419.
S. Patel and B.K. Mishra, Tetrahedron, 63, 4367 (2007); https://doi.org/10.1016/j.tet.2007.02.073.
A.S. Rao, K.C. Rajanna, K.R. Reddy and S. Kulkarni, Synth. React. Inorg. Met.-Org. Nano-Met. Chem., 46, 832 (2016); https://doi.org/10.1080/15533174.2014.989596.
K.C. Rajanna, A.S. Rao, I.E. Chakravarthi and K.R. Reddy, Asian J. Chem., 30, 167 (2018); https://doi.org/10.14233/ajchem.2018.20963.
J.M. Harris, N.H. Hundley, T.G. Shannon and E.C. Struck, J. Org. Chem., 47, 4789 (1982); https://doi.org/10.1021/jo00145a041.
S. Baj and A. Siewniak, Appl. Catal. A Gen., 321, 175 (2007); https://doi.org/10.1016/j.apcata.2007.01.049.
D.J. Heldebrant and P.G. Jessop, J. Am. Chem. Soc., 125, 5600 (2003); https://doi.org/10.1021/ja029131l.
J. Chen, S.K. Spear, J.G. Huddleston and R.D. Rogers, Green Chem., 7, 64 (2005); https://doi.org/10.1039/b413546f.
M. Kidwai, D. Bhatnagar, N.K. Mishra and V. Bansal, Catal. Commun., 9, 2547 (2008); https://doi.org/10.1016/j.catcom.2008.07.010.
(a) B.P. Bandgar, S.A. Patil, B.L. Korbad, S.B. Bandgar and B.S. Hote, Aust. J. Chem., 61, 552 (2008); https://doi.org/10.1071/CH08041. (b) B.P. Bandgar, B.L. Korbad, S.A. Patil, S.B. Bandgar, H.V. Chavan and B.S. Hote, Aust. J. Chem., 61, 700 (2008); https://doi.org/10.1071/CH08106. (c) S.S. Gawande, B.P. Bandgar, P.D. Kadam and S.S. Sable, Green Chem. Lett. Rev., 3, 315 (2010); https://doi.org/10.1080/17518253.2010.486772.
J. Dey and S. Shrivastava, Langmuir, 28, 17247 (2012); https://doi.org/10.1021/la303210f.
B. Das, M. Krishnaiah, P. Balasubramanyam, B. Veeranjaneyulu and D.N. Kumar, Tetrahedron Lett., 49, 2225 (2008); https://doi.org/10.1016/j.tetlet.2008.02.050.
K.C. Rajanna, V.S. Chary, M.S. Kumar, G. Krishnaiah, P. Srinivas, P. Venkanna, M. Venkateswarlu, K. Ramesh, K.R. Reddy and B. Suresh, Green Chem. Lett. Rev., 8, 50 (2015); https://doi.org/10.1080/17518253.2015.1105309.
S. Adimurthy, G. Ramachandraiah, A.V. Bedekar, S. Ghosh, B.C. Ranu and P.K. Ghosh, Green Chem., 8, 916 (2006); https://doi.org/10.1039/b606586d.
W.T. Richards and A.L. Loomis, J. Am. Chem. Soc., 49, 3086 (1927); https://doi.org/10.1021/ja01411a015.
T.J. Mason, Chem. Soc. Rev., 26, 443 (1997); https://doi.org/10.1039/cs9972600443.
V. Singh, K.P. Kaur, A. Khurana and G.L. Kad, Resonance, 3, 56 (1998); https://doi.org/10.1007/BF02836081.
T.J. Mason and D. Peters, Practical Sonochemistry: Power Ultrasound Uses and Applications, Hoorwood Publishing, Chichester, edn 2 (2003).
H. Fillion and J.L. Luche, ed.: J.L. Luche, Selected Experiments, In: Synthetic Organic Sonochemistry, Plenum, New York, Chap. 9 (1998).