Abstract
Amberlyst 15 (A-15) is one of the most common heterogeneous catalysts in organic synthesis. Since its development in 1962, A-15 has proved to be a highly efficient green catalyst in many organic reactions that require acid catalysis. In the last two decades, many reports had been issued that focused on the use of A-15 as a catalyst in heterocyclic synthesis. The use of A-15 implies many advantages as being inexpensive, non-toxic, easily handled, and easily separable from the reaction mixture. Other advantages include easy separation of the products and the recyclability. The latter is highly useful in sustainable chemistry. The present review summarizes the applications of Amberlyst 15 as a green catalyst in the synthesis of heterocycles during the last decade (from 2010 till 2019). The review is classified according to the ring size with a focus on the mechanism of reactions catalyzed by A-15.
Similar content being viewed by others
REFERENCES
Kitanosono, T., Masuda, K., Xu, P., and Kobayashi, S., Chem. Rev., 2018, vol. 118, p. 679. https://doi.org/10.1021/acs.chemrev.7b00417
Wacławek, S., Padil, V.V.T., and Černík, M., Ecol. Chem. Eng. S, 2018, vol. 25, no. 1, p. 9. https://doi.org/10.1515/eces-2018-0001
Kokel, A., Schäfer, C., and Török, B., Curr. Org. Synth., 2019, vol. 16, no. 4, p. 615. https://doi.org/10.2174/1570179416666190206141028
Pal, R., Sarkar, T., and Khasnobis, S., Arkivoc. 2012, vol. 2012, part (i), p. 570. https://doi.org/10.3998/ark.5550190.0013.114
Abrams, I.M. and Milk, J.R., React. Funct. Polym., 1997, vol. 35, p. 7. https://doi.org/10.1016/S1381-5148(97)00058-8
Kunin, R., Meitzner, E., Oline, J., Fischer, S., and Frisch, N., Ind. Eng. Chem. Prod. Res. Dev., 1962, vol. 1, no. 2, p. 140. https://doi.org/10.1021/i360002a016
Corain, B., Zecca, M., and Jeřábek, K., J. Mol. Catal. A: Chem., 2001, vol. 177, no. 1, p. 3. https://doi.org/10.1016/S1381-1169(01)00305-3
Miyazawa, T., Kusunoki, Y., Kunimori, K., and Tomishige, K., J. Catal., 2006, vol. 240, no. 2, p. 213. https://doi.org/10.1016/j.jcat.2006.03.023
Shelkar, R., Singh, A., and Nagarkar, J., Tetrahedron Lett., 2013, vol. 54, no. 1, p. 106. https://doi.org/10.1016/j.tetlet.2012.10.116
Palmieri, A., Gabrielli, S., and Ballini, R., Chem. Commun., 2010, vol. 46, no. 33, p. 6165. https://doi.org/10.1039/c0cc01097a
Shinde, V.M., Patil, G.N., Katariya, A., and Mahajan, Y.S., Chem. Eng. Process., 2015, vol. 95, p. 241. https://doi.org/10.1016/j.cep.2015.06.016
Taylor, R. and Krishna, R., Chem. Eng. Sci., 2000, vol. 55, no. 22, p. 5183. https://doi.org/10.1016/S0009-2509(00)00120-2
Segovia-Hernández, J.G., Hernández, S., and Bonilla Petriciolet, A., Chem. Eng. Process., 2015, vol. 97, p. 134. https://doi.org/10.1016/j.cep.2015.09.004
Gupta, R., Shah, S., and Dubey, S., Imp. J. Interdiscip. Res., 2016, vol. 2, no. 12, p. 314. https://www.onlinejournal.in/IJIRV2I12/051.pdf
Rosatella, A.A., Simeonov, S.P., Frade, R.F.M., and Afonso, C.A.M., Green Chem., 2011, vol. 13, no. 4, p. 754. https://doi.org/10.1039/c0gc00401d
Gallezot, P., Chem. Soc. Rev., 2012, vol. 41, no. 4, p. 1538. https://doi.org/10.1039/c1cs15147a
Fan, W., Verrier, C., Queneau, Y., and Popowycz, F., Curr. Org. Synth., 2019, vol. 16, p. 583. https://doi.org/10.2174/1570179416666190412164738
Zhu, H., Cao, Q., Li, C., and Mua, X., Carbohydr. Res., 2011, vol. 346, no. 13, p. 2016. https://doi.org/10.1016/j.carres.2011.05.026
Takagaki, A., Ohara, M., Nishimura, S., and Ebitani, K., Chem. Commun., 2009, p. 6276. https://doi.org/10.1039/b914087e
Tuteja, J., Nishimura, S., and Ebitani, K., Bull. Chem. Soc. Jpn., 2012, vol. 85, no. 3, p. 275. https://doi.org/10.1246/bcsj.20110287
Jeong, J., Antonyraj, C.A., Shin, S., Kim, S., Kim, B., Lee, K.Y., and Cho, J.K., J. Ind. Eng. Chem., 2013, vol. 19, no. 4, p. 1106. https://doi.org/10.1016/j.jiec.2012.12.004
Aellig, C. and Hermans, I., ChemSusChem, 2012, vol. 5, no. 9, p. 1737. https://doi.org/10.1002/cssc.201200279
Shimizu, K.-i., Uozumi, R., and Satsuma, A., Catal. Commun., 2009, vol. 10, no. 14, p. 1849. https://doi.org/10.1016/j.catcom.2009.06.012
Wang, J., Xu, W., Ren, J., Liu, X., Lu, G., and Wang, Y., Green Chem., 2011, vol. 13, no. 10, p. 2678. https://doi.org/10.1039/c1gc15306d
Lansalot-Matras, C. and Moreau, C., Catal. Commun., 2003, vol. 4, no. 10, p. 517. https://doi.org/10.1016/S1566-7367(03)00133-X
Sampath, G. and Kannan, S., Catal. Commun., 2013, vol. 37, p. 41. https://doi.org/10.1016/j.catcom.2013.03.021
Alonso, D.A., Baeza, A., Chinchilla, R., Guillena, G., Pastor, I.M., and Ramón, D.J., Eur. J. Org. Chem., 2016, vol. 2016, p. 612. https://doi.org/10.1002/ejoc.201501197
Paiva, A., Craveiro, R., Aroso, I., Martins, M., Reis, R.L., and Duarte, A.R.C., ACS Sustainable Chem. Eng., 2014, vol. 2, no. 5, p. 1063. https://doi.org/10.1021/sc500096j
Vanda, H., Dai, Y., Wilson, E.G., Verpoorte, R., and Choi, Y.H., C. R. Chim., 2018, vol. 21, no. 6, p. 628. https://doi.org/10.1016/j.crci.2018.04.002
Liu, Y., Friesen, J.B., McAlpine, J.B., Lankin, D.C., Chen, S.-N., and Paul, G.F., J. Nat. Prod., 2018, vol. 81, no. 3, p. 679. https://doi.org/10.1016/j.physbeh.2017.03.040
Hayyan, M., Hashim, M.A., Hayyan, A., Al-Saadi, M.A., AlNashef, I.M., Mirghani, M.E.S., and Saheed, O.K., Chemosphere, 2013, vol. 90, no. 7, p. 2193. https://doi.org/10.1016/j.chemosphere.2012.11.004
Smith, E.L., Abbott, A.P., and Ryder, K.S., Chem. Rev., 2014, vol. 114, no. 21, p. 11060. https://doi.org/10.1021/cr300162p
Suriyanarayanan, S., Olsson, G.D., Kathiravan, S., Ndizeye, N., and Nicholls, I.A., Int. J. Mol. Sci., 2019, vol. 20, no. 12, p. 2857. https://doi.org/10.3390/ijms20122857
Qin, H., Hu, X., Wang, J., Cheng, H., Chen, L., and Qi, Z., Green Energy Environ., 2020, vol. 5, no. 1, p. 8. https://doi.org/10.1016/j.gee.2019.03.002
Ünlü, A.E., Arlkaya, A., and Takaç, S., Green Process. Synth., 2019, vol. 8, no. 1, p. 355. https://doi.org/10.1515/gps-2019-0003
Marullo, S., Rizzo, C., and D’anna, F., ACS Sustainable Chem. Eng., 2019, vol. 7, no. 15, p. 13359. https://doi.org/10.1021/acssuschemeng.9b02605
Ru, C., Luff, C., Begli, A.H., and Koenig, B., Synth. Commun., 2012, vol. 42, no. 21, p. 3112. https://doi.org/10.1080/00397911.2011.576375
Shirotori, M., Nishimura, S., and Ebitani, K., Catal. Sci. Technol., 2014, vol. 4, no. 4, p. 971. https://doi.org/10.1039/c3cy00980g
Dias, A.S., Pillinger, M., and Valente, A.A., J. Catal., 2005, vol. 229, no. 2, p. 414. https://doi.org/10.1016/j.jcat.2004.11.016
Lanzafame, P., Temi, D.M., Perathoner, S., Spadaro, A.N., and Centi, G., Catal. Today, 2012, vol. 179, no. 1, p. 178. https://doi.org/10.1016/j.cattod.2011.07.018
Jeon, W., Ban, C., Kim, J.E., Woo, H.C., and Kim, D.H., J. Mol. Catal. A: Chem., 2016, vol. 423, p. 264. https://doi.org/10.1016/j.molcata.2016.07.020
Chiurchiù, E., Patehebieke, Y., Gabrielli, S., Ballini, R., and Palmieri, A., Adv. Synth. Catal., 2019, vol. 361, no. 9, p. 2042. https://doi.org/10.1002/adsc.201801660
Murthi, P.R.K., Rambabu, D., Rao, M.V.B., and Pal, M., Tetrahedron Lett., 2014, vol. 55, no. 2, p. 507. https://doi.org/10.1016/j.tetlet.2013.11.073
Aldmairi, A.H., Knight, D.W., and Wirth, T., Synlett, 2017, vol. 28, no. 20, p. 2976. https://doi.org/10.1055/s-0036-1591513
Kumar, A.D., Prabhudeva, M.G., Bharath, S., Kumara, K., Lokanath, N.K., and Kumar, K.A., Bioorg. Chem., 2018, vol. 80, p. 444. https://doi.org/10.1016/j.bioorg.2018.06.023
Prabhudeva, M.G., Kumara, K., Dileep Kumar, A., Ningappa, M.B., Lokanath, N.K., and Ajay Kumar, K., Res. Chem. Intermed., 2018, vol. 44, no. 11, p. 6453. https://doi.org/10.1007/s11164-018-3501-2
Prabhudeva, M.G., Vivek, H.K., and Kumar, K.A., Chem. Data Collect., 2019, vol. 20, article ID 100193. https://doi.org/10.1016/j.cdc.2019.100193
Pandit, S.S., Bhalerao, S.K., Aher, U.S., Adhav, G.L., and Pandit, V.U., J. Chem. Sci., 2011, vol. 123, no. 4, p. 421. https://doi.org/10.1007/s12039-011-0097-0
Nirwan, N. and Pareek, C., Int. J. Sci. Res. Sci. Technol., 2017, vol. 3, no. 8, p. 76. https://doi.org/10.32628/IJSRST173824
Zhang, H., Dong, D.-Q., and Wang, Z.-L., Synthesis, 2016, vol. 48, no. 1, p. 131. https://doi.org/10.1055/s-0035-1560488
Gunduz, H., Kumbaraci, V., Özkılıç, Y., Tüzün, N., and Talinli, N., ChemistrySelect, 2019, vol. 4, no. 24, p. 7278. https://doi.org/10.1002/slct.201901403
Vyskočilová, E., Rezková, L., Vrbková, E., Paterová, I., and Červený, L., Res. Chem. Intermed., 2016, vol. 42, no. 2, p. 725. https://doi.org/10.1007/s11164-015-2052-z
Li, J.J., Name Reactions. A Collection of Detailed Mechanisms and Synthetic Applications, Cham: Springer, 2014, 5th ed. https://doi.org/10.1007/978-3-319-03979-4
Prins, H.J., Chem. Weekbl., 1919, vol. 16, p. 1072.
Gelmini, A., Albonetti, S., Cavani, F., Cesari, C., Lolli, A., Zanotti, V., and Mazzoni, R., Appl. Catal., B, 2016, vol. 180, p. 38. https://doi.org/10.1016/j.apcatb.2015.06.003
Jetti, S.R., Verma, D., and Jain, S., Int. Scholarly Res. Not., 2012, vol. 2012, article ID 480989. https://doi.org/10.5402/2012/480989
Jetti, S.R., Neelaiah Babu, G., Paliwal, P., Bhatewra, A., Kadre, T., and Jain, S., Pharma Chem., 2012, vol. 4, no. 1, p. 417.
Shen, P., Xu, M., Yin, D., Xie, S., Zhou, C., and Li, F., Catal. Commun., 2016, vol. 77, p. 18. https://doi.org/10.1016/j.catcom.2016.01.010
Rambabu, D., Murthi, P.R.K., Dulla, B., Rao, M.V.B., and Pal, M., Synth. Commun., 2013, vol. 43, no. 22, p. 3083. https://doi.org/10.1080/00397911.2013.769605
Guha, C., Sepay, N., and Mallik, A.K., Monatsh. Chem., 2015, vol. 146, no. 8, p. 1349. https://doi.org/10.1007/s00706-014-1401-8
Guha, C., Samanta, S., Sepay, N., and Mallik, A.K., Tetrahedron Lett., 2015, vol. 56, no. 34, p. 4954. https://doi.org/10.1016/j.tetlet.2015.07.005
Sepay, N., Mallik, S., Guha, C., and Mallik, A.K., RSC Adv., 2016, vol. 6, no. 98, p. 96016. https://doi.org/10.1039/c6ra13584f
Samanta, S., Sepay, N., Mallik, S., Mondal, R., Rahaman Molla, M., and Mallik, A.K., Synth. Commun., 2017, vol. 47, no. 23, p. 2195. https://doi.org/10.1080/00397911.2017.1365906
Bouasla, S., Amaro-Gahete, J., Esquivel, D., López, M.I., Jiménez-Sanchidrián, C., Teguiche, M., and Romero-Salguero, F.J., Molecules, 2017, vol. 22, no. 12, p. 2072. https://doi.org/10.3390/molecules22122072
Von Pechmann, H. and Duisberg, C., Ber., 1883, vol. 16, p. 2119. https://doi.org/10.1002/cber.188301602117
Merza, J., Chem. Mater. Res., 2018, vol. 10, no. 3, p. 16.
Hoefnagel, A.J., Gunnewegh, E.A., Downing, R.S., and Van Bekkum, H., J. Chem. Soc., Chem. Commun., 1995, no. 2, p. 225. https://doi.org/10.1039/C39950000225
Khandekar, A.C. and Khadilkar, B.M., Synlett, 2002, vol. 2002, p. 152. https://doi.org/10.1055/s-2002-19332
Nageswar, Y.V.D., Reddy, K.H.V., Ramesh, K., and Murthy, S.N., Org. Prep. Proced. Int., 2013, vol. 45, no. 1, p. 1. https://doi.org/10.1080/00304948.2013.743419
Liu, J.-Y., Liu, J., Wang, J.-D., Jiao, D.-Q., and Liu, H.-W., Synth. Commun., 2010, vol. 40, no. 14, p. 2047. https://doi.org/10.1080/00397910903219401
Chari, M.A., Tetrahedron Lett., 2011, vol. 52, no. 46, p. 6108. https://doi.org/10.1016/j.tetlet.2011.09.015
Shaabani, A., Maleki, A., Mofakham, H., and Khavasi, H.R., J. Comb. Chem., 2008, vol. 10, no. 2, p. 323. https://doi.org/10.1021/cc7001777
Murthy, P.V., Rambabu, D., Krishna, G.R., Reddy, C.M., Prasad, K.R.S., Rao, M.V.B., and Pal, M., Tetrahedron Lett., 2012, vol. 53, no. 7, p. 863. https://doi.org/10.1016/j.tetlet.2011.12.023
Rambabu, D., Kumar, S.K., Sreenivas, B.Y., Sandra, S., Kandale, A., Misra, P., Rao, M.V.B., and Pal, M., Tetrahedron Lett., 2013, vol. 54, no. 6, p. 495. https://doi.org/10.1016/j.tetlet.2012.11.057
Kumar, S.K., Rambabu, D., Kumar, C.H.V., Sreenivas, B.Y., Prasad, K.R.S., Rao, M.V.B., and Pal, M., RSC Adv., 2013, vol. 3, no. 47, p. 24863. https://doi.org/10.1039/c3ra44703k
Jetti, S.R., Bhatewara, A., Kadre, T., and Jain, S., Pharma Chem., 2016, vol. 8, no. 5, p. 98.
Muthukrishnan, I., Vachan, B.S., Karuppasamy, M., Eniyaval, A., Uma Maheswari, C., Nagarajan, S., Menéndez, J.C., and Sridharan, V., Org. Biomol. Chem., 2019, vol. 17, no. 28, p. 6872. https://doi.org/10.1039/c9ob01256g
Patil, V.V. and Shankarling, G.S., Catal. Commun., 2014, vol. 57, p. 138. https://doi.org/10.1016/j.catcom.2014.08.024
Maurya, H.K. and Gupta, A., Tetrahedron Lett., 2014, vol. 55, no. 10, p. 1715. https://doi.org/10.1016/j.tetlet.2014.01.095
Samanta, S., Das Gupta, A., Mondal, R., and Mallik, A.K., J. Chem. Sci., 2013, vol. 125, no. 4, p. 737. https://doi.org/10.1007/s12039-013-0442-6
Hese, S.V., Kamble, R.D., Mogle, P.P., Kamble, S.S., Hebade, M.J., Ambhore, A.N., Kadam, S.N., Gacche, R.N., and Dawane, B.S., J. Chem. Pharm. Res., 2015, vol. 7, no. 7, p. 784.
Pasha, J., Kandagatla, B., Sen, S., Seerapu, G.P.K., Bujji, S., Haldar, D., Nanduri, S., and Oruganti, S., Tetrahedron Lett., 2015, vol. 56, no. 18, p. 2289. https://doi.org/10.1016/j.tetlet.2015.03.078
Povarov, L.S. and Mikhailov, B.M., Bull. Acad. Sci. USSR, Div. Chem. Sci., 1963, vol. 12, p. 871. https://doi.org/10.1007/BF01134751
Kouznetsov, V.V., Tetrahedron, 2009, vol. 65, no. 14, p. 2721. https://doi.org/10.1016/j.tet.2008.12.059
Makioka, Y., Shindo, T., Taniguchi, Y., Takaki, K., and Fujiwara, Y., Synthesis, 1995, vol. 1995, p. 801. https://doi.org/10.1055/s-1995-4002
Niu, Q., Xi, J., Li, L., Li, L., Pan, C., Lan, M., and Rong, L., Tetrahedron Lett., 2019, vol. 60, no. 43, p. 4. https://doi.org/10.1016/j.tetlet.2019.151181
Mazaahir, K., Ritika, C., and Divya, B., Sci. China Chem., 2012, vol. 55, no. 10, p. 2154. https://doi.org/10.1007/s11426-012-4665-z
Wu, L., Zhang, C., and Li, W., Bioorg. Med. Chem. Lett., 2014, vol. 24, no. 6, p. 1462. https://doi.org/10.1016/j.bmcl.2014.02.018
Chaskar, A., Padalkar, V., Phatangare, K., Takale, S., and Murugan, K., Green Chem. Lett. Rev., 2013, vol. 6, no. 3, p. 217. https://doi.org/10.1080/17518253.2012.739209
Xia, Q., Li, C., Zhang, Y., Qi, C., and Zhang, F., ChemistrySelect, 2018, vol. 3, no. 32, p. 9232. https://doi.org/10.1002/slct.201801411
Xu, Z., Du, Y., Wang, S., Wu, Z., Lou, Y., and Zhang, F., J. Heterocycl. Chem., 2019, vol. 56, no. 9, p. 2517. https://doi.org/10.1002/jhet.3646
Li, C., Zhang, F., and Qi, C., Synlett, 2018, vol. 29, no. 20, p. 2707. https://doi.org/10.1055/s-0037-1609655
Satasia, S.P., Kalaria, P.N., and Raval, D.K., Org. Biomol. Chem., 2014, vol. 12, p. 1751. https://doi.org/10.1039/b000000x
Li, C. and Zhang, F., ChemistrySelect, 2018, vol. 3, no. 6, p. 1815. https://doi.org/10.1002/slct.201702942
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The author declares no conflict of interest.
Rights and permissions
About this article
Cite this article
El-Nassan, H.B. Amberlyst 15®: An Efficient Green Catalyst for the Synthesis of Heterocyclic Compounds. Russ J Org Chem 57, 1109–1134 (2021). https://doi.org/10.1134/S1070428021070125
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428021070125