Abstract
Considering the green nature, biocompatibility, novelty, ease of preparation, and unique properties of vitamin-functionalized nanocatalysts, various vitamins have been supported on various nanosupports to be utilized as heterogeneous catalysts. Due to the novelty and synergistic effect of nanocatalysis and organocatalysis, vitamin-functionalized nanocatalysts have been used in various organic reactions, including C–C coupling, oxidation, multicomponent reactions, etc. These heterogeneous nanocatalysts provide chemists with various advantages such as low catalyst loading, nontoxic and easy-to-handle catalyst, shorter reaction time, high yield, elimination of by-products, avoidance of hazardous organic solvents, and easy workup.
REFERENCES
Saghanezhad, S.J., Nazari, Y., and Davod, F., RSC Adv., 2016, vol. 6, p. 25525. https://doi.org/10.1039/C6RA02255C
Kiasat, A., Almasi, H., and Saghanezhad, S.J., Org. Chem. Res., 2015, vol. 1, p. 72. https://doi.org/10.22036/ORG.CHEM..2015.10668
Matthews, J., Torres, S.J., Milte, C.M., Hopkins, I., Kukuljan, S., Nowson, C.A., and Daly, R.M., Eur. J. Nutr., 2020, vol. 59, p. 1081. https://doi.org/10.1007/s00394-019-01969-8
Reyes-Mercado, E., Rivas-Loaiza, J.A., GarcíaMerinos, J.P., López, Y., and González-Campos, J.B., Chem. Eng. Process., 2020, vol. 159, article ID 108201. https://doi.org/10.1016/j.cep.2020.108201
Martin-Jimeno, F.J., Suárez-García, F., Paredes, J.I., Martínez-Alonso, A., and Tascón, J.M., J. Alloys Compd., 2020, vol. 853, article ID 157348. https://doi.org/10.1016/j.jallcom.2020.157348
Fattahi, N., Ramazani, A., Ahankar, H., Asiabi, P.A., and Kinzhybalo, V., Silicon, 2019, vol. 11, p. 1441. https://doi.org/10.1007/s12633-018-9954-5
Neochoritis, C.G., Zarganes-Tzitzikas, T., Katsampoxaki-Hodgetts, K., and Dömling, A., J. Chem. Educ., 2020, vol. 97, p. 3739. https://doi.org/10.1021/acs.jchemed.0c00290
Wdowik, T. and Gryko, D., ACS Catal., 2022, vol. 12, p. 6517. https://doi.org/10.1021/acscatal.2c01596
Fuse, H., Irie, Y., Fuki, M., Kobori, Y., Kato, K., Yamakata, A., and Kanai, M., J. Am. Chem. Soc., 2022, vol. 144, p. 6566. https://doi.org/10.1021/jacs.2c01705
Farsi, R., Mohammadi, M.K. and Saghanezhad, S.J., Res. Chem. Intermed., 2020, vol. 47, p. 1161. https://doi.org/10.1007/s11164-020-04322-5
Xiao, R., Wang, S., Ibrahim, M.H., Abdu, H.I., Shan, D., Chen, J., and Lu, X., J. Chromatogr. A, 2019, vol. 1593, p. 1. https://doi.org/10.1016/j.chroma.2019.02.005
Veisi, H., Pirhayati, M., and Kakanejadifard, A., Tetrahedron Lett., 2017, vol. 58, p. 4269. https://doi.org/10.1016/j.tetlet.2017.09.078
Kudr, J., Haddad, Y., Richtera, L., Heger, Z., Cernak, M., Adam, V., and Zitka, O., Nanomaterials, 2017, vol. 7, article no. 243. https://doi.org/10.3390/nano7090243
Khoshnevisan, K., Vakhshiteh, F., Barkhi, M., Baharifar, H., Poor-Akbar, E., Zari, N., Stamatis, H., and Bordbar, A.K., Mol. Catal., 2017, vol. 442, p. 66. https://doi.org/10.1016/j.mcat.2017.09.006
Ashraf, M.A., Liu, Z., Peng, W.X., and Gao, C., Catal. Lett., 2020, vol. 150, p. 683. https://doi.org/10.1007/s10562-019-02986-2
Rogers, L. and Jensen, K.F., Green Chem., 2019, vol. 21, p. 3481. https://doi.org/10.1039/C9GC00773C
Poliakoff, M. and Licence, P., Nature, 2007, vol. 450, p. 810. https://doi.org/10.1038/450810a
Wu, K., Su, D., Liu, J., Saha, R., and Wang, J.P., Nanotechnology, 2019, vol. 30, article ID 502003. https://doi.org/10.1088/1361-6528/ab4241
Rashid, Z., Soleimani, M., Ghahremanzadeh, R., Vossoughi, M., and Esmaeili, E., Appl. Surf. Sci., 2017, vol. 426, p. 1023. https://doi.org/10.1016/j.apsusc.2017.07.246
Liu, S., Yu, B., Wang, S., Shen, Y., and Cong, H., Adv. Colloid Interface Sci., 2020, vol. 280, article ID 102165. https://doi.org/10.1016/j.cis.2020.102165
Hedayatnasab, Z., Abnisa, F., and Daud, W.M.A.W., Mater. Des., 2017, vol. 123, p. 174. https://doi.org/10.1016/j.matdes.2017.03.036
Bilal, M., Zhao, Y., Rasheed, T., and Iqbal, H.M., Int. J. Biol. Macromol., 2018, vol. 120, p. 2530. https://doi.org/10.1016/j.ijbiomac.2018.09.025
Enders, D. and Balensiefer, T., Acc. Chem. Res., 2004, vol. 37, p. 534. https://doi.org/10.1021/ar030050j
List, B., Chem. Rev., 2007, vol. 107, p. 5413. https://doi.org/10.1021/cr078412e
Wang, Y., Luo, X., Tang, J., Hu, X., Xu, Q., and Yang, C., Anal. Chim. Acta, 2012, vol. 713, p. 92. https://doi.org/10.1016/j.aca.2011.11.022
Wang, J., Zhao, G., and Yu, F., J. Taiwan Inst. Chem. Eng., 2016, vol. 69, p. 139. https://doi.org/10.1016/j.jtice.2016.10.004
Polshettiwar, V. and Varma, R.S., Green Chem., 2010, vol. 12, p. 743. https://doi.org/10.1039/B921171C
Motevalizadeh, S.F., Khoobi, M., Sadighi, A., Khalilvand-Sedagheh, M., Pazhouhandeh, M., Ramazani, A., Faramarzi, M.A., and Shafiee, A., J. Mol. Catal. B: Enzym., 2015, vol. 120, p. 75. https://doi.org/10.1016/j.molcatb.2015.06.013
Ge, N., Xu, J., Li, F., Peng, B., and Pan, S., Food Control, 2017, vol. 82, p. 83. https://doi.org/10.1016/j.foodcont.2017.06.027
de Britto, D., de Moura, M.R., Aouada, F.A., Mattoso, L.H., and Assis, O.B., Food Hydrocolloids, 2012, vol. 27, p. 487. https://doi.org/10.1016/j.foodhyd.2011.09.002
Chauhan, D., Gupta, P.K., and Solanki, P.R., Mater. Sci. Eng., C, 2018, vol. 93, p. 145. https://doi.org/10.1016/j.msec.2018.07.036
Sayahi, M.H., Bahadorikhalili, S., Saghanezhad, S.J., Miller, M.A., and Mahdavi, M., Res. Chem. Intermed., 2020, vol. 46, p. 491. https://doi.org/10.1007/s11164-019-03962-6
Saghanezhad, S.J., Sayahi, M.H., Imanifar, I., Mombeni, M., and Hamood, S.D., Res. Chem. Intermed., 2017, vol. 43, p. 6521. https://doi.org/10.1007/s11164-017-3002-8
Mohammadi, M.K., Saghanezhad, S.J., and Razzaghiasl, N., Bull. Chem. Soc. Ethiop., 2017, vol. 31, p. 535. https://doi.org/10.4314/bcse.v31i3.17
Bodaghifard, M.A., Hamidinasab, M., and Ahadi, N., Curr. Org. Chem., 2018, vol. 22, p. 234. https://doi.org/10.2174/1385272821666170705144854
Fan, P., Liu, C., Hu, C., Li, F., Lin, X., Xiao, F., and Yang, S., New J. Chem., 2022, vol. 46, p. 877. https://doi.org/10.1039/D1NJ04706J
Linster, C.L. and Van Schaftingen, E., FEBS J., 2007, vol. 274, p. 1. https://doi.org/10.1111/j.1742-4658.2006.05607.x
Allen, L.H., Am. J. Clin. Nutr., 2009, vol. 89, p. 693S. https://doi.org/10.3945/ajcn.2008.26947A
Williams, M.T., Morrill, L.C., and Browne, D.L., ChemSusChem, 2022, vol. 15, article ID e202102157. https://doi.org/10.1002/cssc.202102157
Mrówczyński, R., Nan, A., and Liebscher, J., RSC Adv., 2014, vol. 4, p. 5927. https://doi.org/10.1039/C3RA46984K
Kong, Y., Tan, R., Zhao, L., and Yin, D., Green Chem., 2013, vol. 15, p. 2422. https://doi.org/10.1039/C3GC40772A
Bazanov, D.R., Maximova, N.A., Seliverstov, M.Y., Zefirov, N.A., Sosonyuk, S.E., and Lozinskaya, N.A., Russ. J. Org. Chem., 2021, vol. 57, p. 1834. https://doi.org/10.1134/S107042802111004X
Kazemnejadi, M., Sharafi, Z., Mahmoudi, B., Zeinali, A., and Nasseri, M.A., J. Iran. Chem. Soc., 2020, vol. 17, p. 777. https://doi.org/10.1007/s13738-019-01814-z
Ghanimati, M., Abdoli-Senejani, M., Bodaghifard, M.A., and Momeni Isfahani, T., Eurasian Chem. Commun., 2020, vol. 2, p. 688. https://doi.org/10.33945/SAMI/ECC.2020.6.6
Esmaeilpour, M., Javidi, J., and Zandi, M., Mater. Res. Bull., 2014, vol. 55, p. 78. https://doi.org/10.1016/j.materresbull.2014.04.019
Dutta, A., Rahman, N., Khongriah, W., Nongrum, R., Joshi, S.R., and Nongkhlaw, R., ChemistrySelect, 2019, vol. 4, p. 12399. https://doi.org/10.1002/slct.201902279
Baig, R.N., Nadagouda, M.N., and Varma, R.S., Coord. Chem. Rev., 2015, vol. 287, p. 137. https://doi.org/10.1016/j.ccr.2014.12.017
Zhang, Z., Duan, H., Li, S., and Lin, Y., Langmuir, 2010, vol. 26, p. 6676. https://doi.org/10.1021/la904010y
Lu, A.H. and Li, W.C., Chem. Commun., 2005, p. 98. https://doi.org/10.1039/B414146F
Tartaj, P. and Serna, C.J., J. Am. Chem. Soc., 2003, vol, 125, p. 15754. https://doi.org/10.1021/ja0380594
Tartaj, P., Gonzalez-Carreno, T., and Serna, C.J.S., Langmuir, 2002, vol. 18, p. 4556. https://doi.org/10.1021/la025566a
Graf, C., Vossen, D.L., Imhof, A., and van Blaaderen, A., Langmuir, 2003, vol. 19, p. 6693. https://doi.org/10.1021/la0347859
Lei, L., Liu, X., Li, Y., Cui, Y., Yang, Y., and Qin, G., Mater. Chem. Phys., 2011, vol. 125, p. 866. https://doi.org/10.1016/j.matchemphys.2010.09.031
Boele, M.D., van Strijdonck, G.P., De Vries, A.H., Kamer, P.C., de Vries, J.G., and van Leeuwen, P.W., J. Am. Chem. Soc., 2002, vol. 124, p. 1586. https://doi.org/10.1021/ja0176907
Gawali, S.L., Shelar, S.B., Gupta, J., Barick, K., and Hassan, P., Int. J. Biol. Macromol., 2021, vol. 166, p. 851. https://doi.org/10.1016/j.ijbiomac.2020.10.241
Zaidi, S.K.R. and Banu, N., Clin. Chim. Acta, 2004, vol. 340, p. 229. https://doi.org/10.1016/j.cccn.2003.11.003
Esam, Z., Akhavan, M., Bekhradnia, A., Mohammadi, M., and Tourani, S., Catal. Lett., 2020, vol. 150, p. 3112. https://doi.org/10.1007/s10562-020-03216-w
Ashraf, M.A., Liu, Z., Zhang, D., and Alimoradi, A., Appl. Organomet. Chem., 2020, vol. 34, article ID e5668. https://doi.org/10.1002/aoc.5668
Azizi, K. and Heydari, A., RSC Adv., 2014, vol. 4, p. 8812. https://doi.org/10.1039/C3RA46437G
Nongrum, R., Nongthombam, G.S., Kharkongor, M., Rahman, N., Kathing, C., Myrboh, B., and Nongkhlaw, R., RSC Adv., 2016, vol. 6, p. 108384. https://doi.org/10.1039/C6RA24108E
Rashidizadeh, A., Ghafuri, H., Esmaili Zand, H.R., and Goodarzi, N., ACS Omega, 2019, vol. 4, p. 12544. https://doi.org/10.1021/acsomega.9b01635
Abbasi, F., Abdoli-Senejani, M., and Azizi, N., React. Kinet., Mech. Catal., 2017, vol. 122, p. 193. https://doi.org/10.1007/s11144-017-1199-6
Azizi, N., Abbasi, F., and Abdoli-Senejani, M., Mater. Chem. Phys., 2017, vol. 196, p. 118. https://doi.org/10.1016/j.matchemphys.2017.04.041
Ghafuri, H., Joorabchi, N., Emami, A., and Esmaili Zand, H.R., Ind. Eng. Chem. Res., 2017, vol. 56, p. 6462. https://doi.org/10.1021/acs.iecr.7b00182
Esfandiary, N., Pazoki, F., Nakisa, A., Azizi, K., Radfar, I., and Heydari, A., Appl. Organomet. Chem., 2020, vol. 34, article ID e5725. https://doi.org/10.1002/aoc.5725
Rafiee, F. and Mehdizadeh, N., Catal. Lett., 2018, vol. 148, p. 1345. https://doi.org/10.1007/s10562-018-2363-y
Shaterian, H.R. and Molaei, P., Appl. Organomet. Chem., 2019, vol. 33, article ID e4964. https://doi.org/10.1002/aoc.4964
Hou, F., Zheng, W., and Yousefi, N., Bull. Chem. React. Eng. Catal., 2020, vol. 15, p. 199. https://doi.org/10.9767/bcrec.15.1.6179.199-212
Kurtan, U., Amir, M., and Baykal, A., Chin. J. Catal., 2015, vol. 36, p. 705. https://doi.org/10.1016/S1872-2067(14)60316-8
Afradi, M., Pour, S.A., Dolat, M., and Yazdani‐Elah‐Abadi, A., Appl. Organomet. Chem., 2018, vol. 32, article ID e4103. https://doi.org/10.1002/aoc.4103
Rezapour, E., Jafarpour, M., and Rezaeifard, A., Catal. Lett., 2018, vol. 148, p. 3165. https://doi.org/10.1007/s10562-018-2513-2
Khazaei, A., Tavasoli, M., and Moosavi-Zare, A.R., Res. Chem. Intermed., 2018, vol. 44, p. 5893. https://doi.org/10.1007/s11164-018-3462-5
Foroughi Kaldareh, M., Mokhtary, M., and Nikpassand, M., Appl. Organomet. Chem., 2020, vol. 34, article ID e5469. https://doi.org/10.1002/aoc.5469
Alishahi, N., Nasr‐Esfahani, M., Mohammadpoor‐Baltork, I., Tangestaninejad, S., Mirkhani, V., and Moghadam, M., Appl. Organomet. Chem., 2020, vol. 34, article ID e5681. https://doi.org/10.1002/aoc.5681
Khazaei, A., Gohari-Ghalil, F., Tavasoli, M., Rezaei-Gohar, M., and Moosavi-Zare, A.R., Chem. Methodol., 2020, vol. 4, p. 543. https://doi.org/10.22034/chemm.2020.106433
Bagheri, S., Pazoki, F., Esfandiary, N., Fadaei, M.M., and Heydari, A., Appl. Organomet. Chem., 2020, vol. 34, article ID e5723. https://doi.org/10.1002/aoc.5723
Farzaneh, F., Taghavi, J., Malakooti, R., and Ghandi, M., J. Mol. Catal. A: Chem., 2006, vol. 244, p. 252. https://doi.org/10.1016/j.molcata.2005.08.058
Shaabani, A., Rashidi Vahid, A., Shaabani, S., Mohammadian, R., Nazeri, M.T., and Keramati Nejad, M., Appl. Organomet. Chem., 2018, vol. 32, article ID e4510. https://doi.org/10.1002/aoc.4510
Hajipour, A.R., Check, M., and Khorsandi, Z., Appl. Organomet. Chem., 2017, vol. 31, article ID e3769. https://doi.org/10.1002/aoc.3769
Pourmorteza, N., Jafarpour, M., Feizpour, F., and Rezaeifard, A., RSC Adv., 2020, vol. 10, p. 12053. https://doi.org/10.1039/D0RA00075B
Suksiriworapong, J., Sripha, K., Kreuter, J., and Junyaprasert, V.B., Bioconjugate Chem., 2011, vol. 22, p. 582. https://doi.org/10.1021/bc100270m
Suksiriworapong, J., Sripha, K., Kreuter, J., and Junyaprasert, V.B., Int. J. Pharm., 2012, vol. 423, p. 562. https://doi.org/10.1016/j.ijpharm.2011.11.033
Thepphankulngarm, N., Wonganan, P., Sapcharoenkun, C., Tuntulani, T., and Leeladee, P., New. J. Chem., 2017, vol. 41, p. 13823. https://doi.org/10.1039/C7NJ02754K
Amir, M., Kurtan, U., and Baykal, A., Chin. J. Catal., 2015, vol. 36, p. 1280. https://doi.org/10.1016/S1872-2067(15)60879-8
Zdarta, J., Meyer, A.S., Jesionowski, T., and Pinelo, M., Catalysts, 2018, vol. 8, article no. 92. https://doi.org/10.3390/catal8020092
Franconetti, A. and de Gonzalo, G., ChemCatChem, 2018, vol. 10, p. 5554. https://doi.org/10.1002/cctc.201801459
Duchemin, N., Org. Biomol. Chem., 2017, vol. 15, p. 7072. https://doi.org/10.1039/C7OB00176B
Bilal, M., Asgher, M., Cheng, H., Yan, Y., and Iqbal, H.M., Crit. Rev. Biotechnol., 2019, vol. 39, p. 202. https://doi.org/10.1080/07388551.2018.1531822
Verma, M.L., Puri, M., and Barrow, C.J., Crit. Rev. Biotechnol., 2016, vol. 36, p. 108. https://doi.org/10.3109/07388551.2014.928811
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Farsi, R., Fallah-Mehrjardi, M., Saghanezhad, S.J. et al. Catalytic Applications of Vitamin-Supported Nanoparticles in Organic Chemistry. Russ J Org Chem 59, 503–520 (2023). https://doi.org/10.1134/S1070428023030193
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DOI: https://doi.org/10.1134/S1070428023030193