Copyright (c) 2022 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Silica Supported Acids (HClO4-SiO2, KHSO4-SiO2) as Eco-friendly Reusable Catalysts for Bromodecarboxylation of α,β-Unsaturated Carboxylic Acids using KBr under Solvothermal and Solvent-Free Conditions
Corresponding Author(s) : Samba Shiva Rao Arisha
Asian Journal of Chemistry,
Vol. 34 No. 3 (2022): Vol 34 Issue 3, 2022
Abstract
A mild procedure has been developed for the bromodecarboxylation of α,β-carboxylic acids using nano silica supported SiO2-HClO4, SiO2-KHSO4 as catalysts and KBr as a bromine source in conventional solvothermal, ultrasonic assisted and solvent-free microwave assisted conditions. The α,β-unsaturated cinnamic acids were converted to corresponding β-bromo styrenes with high regioselectivity, while aliphatic α,β-unsaturated carboxylic acids afforded related β-bromo alkenes.
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- A. Varenikov, E. Shapiro and M. Gandelman, Chem. Rev., 121, 412 (2021); https://doi.org/10.1021/acs.chemrev.0c00813
- P. Camps, A.E. Lukach, X. Pujol and S. Vázquez, Tetrahedron, 56, 2703 (2000); https://doi.org/10.1016/S0040-4020(00)00169-1
- J.M. Quibell, G.J.P. Perry, D.M. Cannas and I. Larrosa, Chem. Sci., 9, 3860 (2018); https://doi.org/10.1039/c8sc01016a
- R.C. Larock, In Comprehensive Organic Transformation: A Guide to Functional Group Preparation; Wiley-VCH: New York, p. 629 (1999).
- S. Chowdhury and S. Roy, Tetrahedron Lett., 37, 2623 (1996); https://doi.org/10.1016/0040-4039(96)00343-7
- D. Naskar, S. Chowdhury and S. Roy, Tetrahedron Lett., 39, 702 (1998); https://doi.org/10.1016/S0040-4039(97)10639-6
- D. Naskar and S. Roy, J. Org. Chem., 64, 6896 (1999); https://doi.org/10.1021/jo990434g
- D. Naskar and S. Roy, J. Chem. Soc., Perkin Trans. I, 2435 (1999); https://doi.org/10.1039/A904515E
- D. Naskar and S. Roy, Tetrahedron, 56, 1369 (2000); https://doi.org/10.1016/S0040-4020(99)01035-2
- D. Naskar, S.K. Das, L. Giribabu, B.G. Maiya and S. Roy, Organometallics, 19, 1464 (2000); https://doi.org/10.1021/om000020+
- J.P. Das and S. Roy, J. Org. Chem., 67, 7861 (2002); https://doi.org/10.1021/jo025868h
- 10 S.C. Roy, C. Guin and G. Maiti, Tetrahedron Lett., 42, 9253 (2001); https://doi.org/10.1016/S0040-4039(01)01936-0
- F. Homsi and G. Rousseau, Tetrahedron Lett., 40, 1495 (1999); https://doi.org/10.1016/S0040 4039(99)00021-0
- F. Homsi and G. Rousseau, J. Org. Chem., 64, 81 (1998); https://doi.org/10.1021/jo9810361
- C. Kuang, H. Senboku and M. Tokuda, Synlett, 1439 (2000); https://doi.org/10.1055/s-2000-7658
- C. Kuang, Q. Yang, H. Senboku and M. Tokuda, Synthesis, 1319 (2005); https://doi.org/10.1055/s-2005-865283
- K.C. Rajanna, N. Reddy, M.R. Reddy and P.K. Saiprakash, J. Dispers. Sci. Technol., 28, 613 (2007); https://doi.org/10.1080/01932690701282690
- J.P. Das, P. Sinha and S. Roy, Org. Lett., 4, 3055 (2002); https://doi.org/10.1021/ol0262901
- S. Ramgopal, K. Ramesh, A. Chakradhar, N.M. Reddy and K.C. Rajanna, Tetrahedron Lett., 48, 4043 (2007); https://doi.org/10.1016/j.tetlet.2007.04.026
- H.H. Kinfe, F.M. Mebrahtu and P.T. Moshapo, Synth. Commun., 43, 1237 (2013); https://doi.org/10.1080/00397911.2011.629068
- Z.N. Siddiqui, F. Farooq, J. Mol. Catal. A Chem., 363-364, 451 (2012); https://doi.org/10.1016/j.molcata.2012.07.024
- M.T. Maghsoodlou, R. Heydari, S.M. Habibi-Khorassani, N. Hazeri, S.S. Sajadikhah, M. Rostamizadeh and M. Lashkari, Synth. Commun., 42, 136 (2012); https://doi.org/10.1080/00397911.2010.523153
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- B. Das, B. Ravikanth, K. Laxminarayana and B.V. Rao, J. Mol. Catal. Chem., 253, 92 (2006); https://doi.org/10.1016/j.molcata.2006.03.007
- B. Das and J. Banerjee, Chem. Lett., 33, 960 (2004); https://doi.org/10.1246/cl.2004.960
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- B.P. Bandgar, S.S. Gawande and D.B. Muley, Green Chem. Lett. Rev., 3, 49 (2010); https://doi.org/10.1080/17518250903447118
- M. Maheswara, V. Siddaiah, G.L.V. Damu and C.V. Rao, ARKIVOC, 201 (2006); https://doi.org/10.3998/ark.5550190.0007.223
- Y. Du, G. Wei, S. Cheng, Y. Hua and R.J. Linhardt, Tetrahedron Lett., 47, 307 (2006); https://doi.org/10.1016/j.tetlet.2005.11.025
- Y.L.N. Murthy and S. Bhagavathula, Chem. Sci. Trans., 2, 805 (2013).
- B.M. Choudary, Y. Sudha and P.N. Reddy, Synlett, 450 (1994); https://doi.org/10.1055/s-1994-22886
- J.R. Hanson, A. Opakunle and P.J. Petit, J. Chem. Res. (S), 457 (1995).
- B.P. Bandgar and N.J. Nigal, Synth. Commun., 28, 3225 (1998); https://doi.org/10.1080/00397919808004426
- B.V. Tamhankar, U.V. Desai, R.B. Mane, P.P. Wadgaonkar and A.V. Bedekar, Synth. Commun., 31, 2021 (2001); https://doi.org/10.1081/SCC-100104419
- N. Narender, P. Srinivasu, M. Ramakrishna Prasad, S.J. Kulkarni and K.V. Raghavan, Synth. Commun., 32, 2313 (2002); https://doi.org/10.1081/SCC-120006001
- A.R. Hajipour, S.E. Mallakpour and H. Adibi, Chem. Lett., 29, 460 (2000); https://doi.org/10.1246/cl.2000.460
- A.R. Hajipour, S.E. Mallakpour and H. Adibi, Chem. Lett., 30, 164 (2001); https://doi.org/10.1246/cl.2001.164
- A.R. Hajipour, S.E. Mallakpour, I.M. Baltork and H. Adibi, Synth. Commun., 31, 3401 (2001); https://doi.org/10.1081/SCC-100106197
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- A.R. Hajipour, S.E. Mallakpour, I. Mohammadpoor-Baltork and H. Adibi, Phosphorus Sulfur Silicon Rel. Elem., 177, 2805 (2002); https://doi.org/10.1080/10426500214884
- Z.N. Siddiqui, Arab. J. Chem., 12, 2788 (2019); https://doi.org/10.1016/j.arabjc.2015.06.013
- C.R. Kamatala, Y. Hemanth Sriram, T. Fatima, S.K. Mukka, K. C. Rajanna, M. Venkateswarlu, M.S. Sudhakar and R.M. Raju, Iran. Chem. Commun, 5, 352 (2017).
- C.R. Kamatala, Asian J. Green Chem., 2, 69 (2017); https://doi.org/10.22631/ajgc.2017.95574.1016
- S. Mishra and R. Ghosh, Synthesis, 21, 3463 (2011); https://doi.org/10.1055/s-0030-1260255
- P. Anastas and J. Warner, Green Chemistry: Theory and Practice; Oxford University Press: New York (1998).
- T.J. Mason and J.P. Lorimer, Sonochemistry: Theory, Applications and Uses of Ultrasound in Chemistry, Ellis Horwood Ltd., Chichester, p. 1150 (1988).
- K.S. Suslick, Ultrasound, it’s Chemical, Physical and Biological Effects, VCH Publishers., Inc. (1988).
- V. Singh, K.P. Kaur, A. Khurana and G.L. Kad, Resonance, 3, 56 (1998); https://doi.org/10.1007/BF02836081
- V. Polshettiwar and R.S. Varma, Chem. Soc. Rev., 37, 1546 (2008); https://doi.org/10.1039/b716534j
- P. Lidström, J. Tierney, B. Wathey and J. Westman, Tetrahedron, 57, 9225 (2001); https://doi.org/10.1016/S0040-4020(01)00906-1
- R.S. Varma, Green Chem., 1, 43 (1999); https://doi.org/10.1039/a808223e
- C.O. Kappe, Angew. Chem. Int. Ed., 43, 6250 (2004); https://doi.org/10.1002/anie.200400655
References
A. Varenikov, E. Shapiro and M. Gandelman, Chem. Rev., 121, 412 (2021); https://doi.org/10.1021/acs.chemrev.0c00813
P. Camps, A.E. Lukach, X. Pujol and S. Vázquez, Tetrahedron, 56, 2703 (2000); https://doi.org/10.1016/S0040-4020(00)00169-1
J.M. Quibell, G.J.P. Perry, D.M. Cannas and I. Larrosa, Chem. Sci., 9, 3860 (2018); https://doi.org/10.1039/c8sc01016a
R.C. Larock, In Comprehensive Organic Transformation: A Guide to Functional Group Preparation; Wiley-VCH: New York, p. 629 (1999).
S. Chowdhury and S. Roy, Tetrahedron Lett., 37, 2623 (1996); https://doi.org/10.1016/0040-4039(96)00343-7
D. Naskar, S. Chowdhury and S. Roy, Tetrahedron Lett., 39, 702 (1998); https://doi.org/10.1016/S0040-4039(97)10639-6
D. Naskar and S. Roy, J. Org. Chem., 64, 6896 (1999); https://doi.org/10.1021/jo990434g
D. Naskar and S. Roy, J. Chem. Soc., Perkin Trans. I, 2435 (1999); https://doi.org/10.1039/A904515E
D. Naskar and S. Roy, Tetrahedron, 56, 1369 (2000); https://doi.org/10.1016/S0040-4020(99)01035-2
D. Naskar, S.K. Das, L. Giribabu, B.G. Maiya and S. Roy, Organometallics, 19, 1464 (2000); https://doi.org/10.1021/om000020+
J.P. Das and S. Roy, J. Org. Chem., 67, 7861 (2002); https://doi.org/10.1021/jo025868h
10 S.C. Roy, C. Guin and G. Maiti, Tetrahedron Lett., 42, 9253 (2001); https://doi.org/10.1016/S0040-4039(01)01936-0
F. Homsi and G. Rousseau, Tetrahedron Lett., 40, 1495 (1999); https://doi.org/10.1016/S0040 4039(99)00021-0
F. Homsi and G. Rousseau, J. Org. Chem., 64, 81 (1998); https://doi.org/10.1021/jo9810361
C. Kuang, H. Senboku and M. Tokuda, Synlett, 1439 (2000); https://doi.org/10.1055/s-2000-7658
C. Kuang, Q. Yang, H. Senboku and M. Tokuda, Synthesis, 1319 (2005); https://doi.org/10.1055/s-2005-865283
K.C. Rajanna, N. Reddy, M.R. Reddy and P.K. Saiprakash, J. Dispers. Sci. Technol., 28, 613 (2007); https://doi.org/10.1080/01932690701282690
J.P. Das, P. Sinha and S. Roy, Org. Lett., 4, 3055 (2002); https://doi.org/10.1021/ol0262901
S. Ramgopal, K. Ramesh, A. Chakradhar, N.M. Reddy and K.C. Rajanna, Tetrahedron Lett., 48, 4043 (2007); https://doi.org/10.1016/j.tetlet.2007.04.026
H.H. Kinfe, F.M. Mebrahtu and P.T. Moshapo, Synth. Commun., 43, 1237 (2013); https://doi.org/10.1080/00397911.2011.629068
Z.N. Siddiqui, F. Farooq, J. Mol. Catal. A Chem., 363-364, 451 (2012); https://doi.org/10.1016/j.molcata.2012.07.024
M.T. Maghsoodlou, R. Heydari, S.M. Habibi-Khorassani, N. Hazeri, S.S. Sajadikhah, M. Rostamizadeh and M. Lashkari, Synth. Commun., 42, 136 (2012); https://doi.org/10.1080/00397911.2010.523153
M.A. Chari and K. Syamasundar, J. Mol. Catal. A Chem., 221, 137 (2004); https://doi.org/10.1016/S1381-1169(04)00595-3
M.A. Chari and K. Syamasundar, Catal. Commun., 6, 624 (2005); https://doi.org/10.1016/j.catcom.2005.03.010
B. Das, B. Ravikanth, K. Laxminarayana and B.V. Rao, J. Mol. Catal. Chem., 253, 92 (2006); https://doi.org/10.1016/j.molcata.2006.03.007
B. Das and J. Banerjee, Chem. Lett., 33, 960 (2004); https://doi.org/10.1246/cl.2004.960
A.T. Khan, L. H.Choudhury and S. Ghosh, J. Mol. Catal. Chem., 255, 230 (2006); https://doi.org/10.1016/j.molcata.2006.04.008
M.A. Bigdeli, M.M. Heravi and G.H. Mahdavinia, J. Mol. Catal. Chem., 275, 25 (2007); https://doi.org/10.1016/j.molcata.2007.05.007
A.M. Bigdeli, F. Nemati and G.H. Mahdavinia, Tetrahedron Lett., 48, 6801 (2007); https://doi.org/10.1016/j.tetlet.2007.07.088
B.P. Bandgar, S.S. Gawande and D.B. Muley, Green Chem. Lett. Rev., 3, 49 (2010); https://doi.org/10.1080/17518250903447118
M. Maheswara, V. Siddaiah, G.L.V. Damu and C.V. Rao, ARKIVOC, 201 (2006); https://doi.org/10.3998/ark.5550190.0007.223
Y. Du, G. Wei, S. Cheng, Y. Hua and R.J. Linhardt, Tetrahedron Lett., 47, 307 (2006); https://doi.org/10.1016/j.tetlet.2005.11.025
Y.L.N. Murthy and S. Bhagavathula, Chem. Sci. Trans., 2, 805 (2013).
B.M. Choudary, Y. Sudha and P.N. Reddy, Synlett, 450 (1994); https://doi.org/10.1055/s-1994-22886
J.R. Hanson, A. Opakunle and P.J. Petit, J. Chem. Res. (S), 457 (1995).
B.P. Bandgar and N.J. Nigal, Synth. Commun., 28, 3225 (1998); https://doi.org/10.1080/00397919808004426
B.V. Tamhankar, U.V. Desai, R.B. Mane, P.P. Wadgaonkar and A.V. Bedekar, Synth. Commun., 31, 2021 (2001); https://doi.org/10.1081/SCC-100104419
N. Narender, P. Srinivasu, M. Ramakrishna Prasad, S.J. Kulkarni and K.V. Raghavan, Synth. Commun., 32, 2313 (2002); https://doi.org/10.1081/SCC-120006001
A.R. Hajipour, S.E. Mallakpour and H. Adibi, Chem. Lett., 29, 460 (2000); https://doi.org/10.1246/cl.2000.460
A.R. Hajipour, S.E. Mallakpour and H. Adibi, Chem. Lett., 30, 164 (2001); https://doi.org/10.1246/cl.2001.164
A.R. Hajipour, S.E. Mallakpour, I.M. Baltork and H. Adibi, Synth. Commun., 31, 3401 (2001); https://doi.org/10.1081/SCC-100106197
A.R. Hajipour, S.E. Mallakpour and H. Adibi, Phosphorus Sulfur Silicon Rel. Elem., 177, 2277 (2002); https://doi.org/10.1080/10426500214100
A.R. Hajipour, S.E. Mallakpour, I. Mohammadpoor-Baltork and H. Adibi, Phosphorus Sulfur Silicon Rel. Elem., 177, 2805 (2002); https://doi.org/10.1080/10426500214884
Z.N. Siddiqui, Arab. J. Chem., 12, 2788 (2019); https://doi.org/10.1016/j.arabjc.2015.06.013
C.R. Kamatala, Y. Hemanth Sriram, T. Fatima, S.K. Mukka, K. C. Rajanna, M. Venkateswarlu, M.S. Sudhakar and R.M. Raju, Iran. Chem. Commun, 5, 352 (2017).
C.R. Kamatala, Asian J. Green Chem., 2, 69 (2017); https://doi.org/10.22631/ajgc.2017.95574.1016
S. Mishra and R. Ghosh, Synthesis, 21, 3463 (2011); https://doi.org/10.1055/s-0030-1260255
P. Anastas and J. Warner, Green Chemistry: Theory and Practice; Oxford University Press: New York (1998).
T.J. Mason and J.P. Lorimer, Sonochemistry: Theory, Applications and Uses of Ultrasound in Chemistry, Ellis Horwood Ltd., Chichester, p. 1150 (1988).
K.S. Suslick, Ultrasound, it’s Chemical, Physical and Biological Effects, VCH Publishers., Inc. (1988).
V. Singh, K.P. Kaur, A. Khurana and G.L. Kad, Resonance, 3, 56 (1998); https://doi.org/10.1007/BF02836081
V. Polshettiwar and R.S. Varma, Chem. Soc. Rev., 37, 1546 (2008); https://doi.org/10.1039/b716534j
P. Lidström, J. Tierney, B. Wathey and J. Westman, Tetrahedron, 57, 9225 (2001); https://doi.org/10.1016/S0040-4020(01)00906-1
R.S. Varma, Green Chem., 1, 43 (1999); https://doi.org/10.1039/a808223e
C.O. Kappe, Angew. Chem. Int. Ed., 43, 6250 (2004); https://doi.org/10.1002/anie.200400655