Abstract
This paper reports the efficient transfer hydrogenation of nitroarenes to anilines using immobilized palladium nanoparticles on a silica–starch substrate (PNP-SSS) in the presence of sodium borohydride as a reducing agent in water as a green solvent at room temperature. The prepared PNP-SSS nanocatalyst was characterized using FT-IR, XRD, SEM, EDS, BET, TEM, and ICP analyses. This catalyst system was found to be a powerful heterogeneous catalyst system to reduce the aromatic nitro compounds yielding anilines with high conversion rates. In this process, the PNP-SSS catalyst can be reused more than five times with almost consistent efficiency.
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Li X, Zhang X, Xu Y, Yu P (2020) Sep Purif Technol 242:116792
Wilcox RJ, Folmer JC, Kennemur JG, Martin JD (2016) Polyhedron 103:35
Dehghani-Firouzabadi AA, Sobhani M, Notash B (2016) Polyhedron 119:49
Ezenyilimba FC, LaDuca RL (2020) Polyhedron 175:114245
Liu H-Y, Gao G-M, Liu J, Wang H-Y (2018) Polyhedron 152:11
Guo X, Li Y, Peng Q, Duan Z, Li M, Shao M, He X (2017) Polyhedron 133:238
Sadjadi S, Kahangi FG, Heravi MM (2020) Polyhedron 175:114210
Kazi SA, Campi EM, Hearn MT (2018) Tetrahedron 74:1731
LaDuca AR, Przybyla JJ, Porta AR, LaDuca RL (2019) Polyhedron 165:143
Xiao Q, Sarina S, Waclawik ER, Jia J, Chang J, Riches JD, Wu H, Zheng Z, Zhu H (2016) ACS Catal 6:1744
Wang K, Guengerich FP (2013) Chem Res Toxicol 26:993
Downing R, Kunkeler P, Van Bekkum H (1997) Catal Today 37:121
Zhang L, Zhou M, Wang A, Zhang T (2019) Chem Rev 120:683
Dong Z, Pan H, Gao P, Xiao Y, Fan L, Chen J, Wang W (2022) Catal Lett 152:299
Dong Z, Pan H, Chen J, Fan L, Guo J, Wang W (2021) J Saudi Chem Soc 25:101317
Samec JS, Bäckvall J-E, Andersson PG, Brandt P (2006) Chem Soc Rev 35:237
Tafesh AM, Weiguny J (1996) Chem Rev 96:2035
Zhang Y, Zhang N, Tang Z-R, Xu Y-J (2013) ACS Sustain Chem Eng 1:1258
Climent MJ, Corma A, Iborra S, Marti L (2015) ACS Catal 5:157
Tomkins P, Gebauer-Henke E, Leitner W, Müller TE (2015) ACS Catal 5:203
Dey R, Mukherjee N, Ahammed S, Ranu BC (2012) Chem Commun 48:7982
Aazza M, Ahlafi H, Moussout H, Mounir C, Fadel A, Addad A (2020) J Environ Chem Eng 8:103707
Zhang P, Shao C, Zhang Z, Zhang M, Mu J, Guo Z, Liu Y (2011) Nanoscale 3:3357
Arai N, Onodera N, Dekita A, Hori J, Ohkuma T (2015) Tetrahedron Lett 56:3913
Dong J, Jin B, Sun P (2014) Org Lett 16:4540
Rai RK, Mahata A, Mukhopadhyay S, Gupta S, Li P-Z, Nguyen KT, Zhao Y, Pathak B, Singh SK (2014) Inorg Chem 53:2904
Cantillo D, Moghaddam MM, Kappe CO (2013) J Org Chem 78:4530
Demirci UB, Akdim O, Andrieux J, Hannauer J, Chamoun R, Miele P (2010) Fuel Cells 10:335
Chinnappan A, Kang H-C, Kim H (2011) Energy 36:755
Bai Y, Wu C, Wu F, Yi B (2006) Mater Lett 60:2236
Huff C, Long JM, Heyman A, Abdel-Fattah TM (2018) ACS Appl Energy Mater 1:4635
Netskina OV, Kochubey DI, Prosvirin IP, Kellerman DG, Simagina VI, Komova OV (2014) J Mol Catal A Chem 390:125
Crisafulli C, Scirè S, Salanitri M, Zito R, Calamia S (2011) Int J Hydrog Energy 36:3817
Zhang Q, Wu Y, Sun X, Ortega J (2007) Ind Eng Chem Res 46:1120
Kiamehr M, Alipour B, Nasrollahzadeh M, Sajadi SM (2018) IET Nanobiotechnol 12:217
Shokouhimehr M, Yek SM-G, Nasrollahzadeh M, Kim A, Varma RS (2019) Appl Sci 9:4183
Mathew JP, Srinivasan M (1992) Polym Int 29:179
Chen Y, Qiu J, Wang X, Xiu J (2006) J Catal 242:227
Polshettiwar V, Len C, Fihri A (2009) Coord Chem Rev 253:2599
Liu S, Zhou Q, Jiang H (2010) Chin J Chem 28:589
Huang H, Yang X (2003) Colloids Surf A Physicochem Eng Asp 226:77
Adlim M, Bakar MA, Liew KY, Ismail J (2004) J Mol Catal A: Chem 212:141
Zhou P, Wang H, Yang J, Tang J, Sun D, Tang W (2012) Ind Eng Chem Res 51:5743
Wu H, Wu C, He Q, Liao X, Shi B (2010) Mater Sci Eng C 30:770
Firouzabadi H, Iranpoor N, Ghaderi A (2011) Org Biomol Chem 9:865
de Souza JF, da Silva GT, Fajardo AR (2017) Carbohydr Polym 161:187
Han H-S, Jiang S-N, Huang M-Y, Jiang Y-Y (1996) Polym Adv Technol 7:704
Gholinejad M, Dasvarz N, Shojafar M, Sansano JM (2019) Inorg Chim Acta 495:118965
Nariya P, Das M, Shukla F, Thakore S (2020) J Mol Liq 300:112279
Khalafi-Nezhad A, Panahi F (2011) Green Chem 13:2408
Khalafi-Nezhad A, Panahi F (2012) J Organomet Chem 717:141
Panahi F, Daneshgar F, Haghighi F, Khalafi-Nezhad A (2017) J Organomet Chem 851:210
Hemmati S, Heravi MM, Karmakar B, Veisi H (2021) Sci Rep 11:1
Vahedi-Notash N, Heravi MM, Alhampour A, Mohammadi P (2020) Sci Rep 10:1
Sadjadi S, Akbari M, Léger B, Monflier E, Heravi MM (2019) ACS Sustain Chem Eng 7:6720
Sharghi H, Beyzavi MH, Doroodmand MM (2008) Eur J Org Chem 2008:4126
Firouzabadi H, Iranpoor N, Karimi B, Hazarkhani H (2000) Synlett 2000:263
Martínez S, Moreno-Mañas M, Vallribera A, Schubert U, Roig A, Molins E (2006) New J Chem 30:1093
Firouzabadi H, Iranpoor N, Gholinejad M (2009) Tetrahedron 65:7079
Sing KS (1985) Pure Appl Chem 57:603
Gowda S, Kempe Gowda BK, Channe Gowda D (2003) Synth Commun 33:281
Kandathil V, Koley TS, Manjunatha K, Dateer RB, Keri RS, Sasidhar B, Patil SA, Patil SA (2018) Inorg Chim Acta 478:195
Kiani Z, Zhiani R, Khosroyar S, Motavalizadehkakhky A, Hosseiny M (2021) Inorg Chem Commun 124:108382
Chang F, Kim H, Lee B, Park S, Park J (2010) Tetrahedron Lett 51:4250
Zheng XL, Zhang YM (2002) Chin J Chem 20:925
Islam M, Mondal P, Roy AS, Tuhina K (2010) Transit Met Chem 35:427
Kim E, Jeong HS, Kim BM (2014) Catal Commun 45:25
Goyal V, Sarki N, Natte K, Ray A (2021) J Indian Chem Soc 98:100014
Brahmayya M, Samsonu D, Murthy Y, Govindh B (2018) South Afr J Chem Eng 25:110
Azadi S, Sardarian AR, Esmaeilpour M (2021) Monatsh Chem 152:809
Kumar A, Purkait K, Dey SK, Sarkar A, Mukherjee A (2014) RSC Adv 4:35233
Kumar BS, Amali AJ, Pitchumani K (2016) J Mol Catal A Chem 423:511
Sreedhar B, Devi DK, Yada D (2011) Catal Commun 12:1009
Liu X, Wang C, Cheng S, Shang N, Gao S, Feng C, Wang C, Qiao Y, Wang Z (2018) Catal Commun 108:103
Zhang L, Liu X, Zhou X, Gao S, Shang N, Feng C, Wang C (2018) ACS Omega 3:10843
Jiang L, Zhang Z (2016) Int J Hydrog Energy 41:22983
Mahata A, Rai RK, Choudhuri I, Singh SK, Pathak B (2014) Phys Chem Chem Phys 16:26365
Goswami A, Kadam RG, Tuček J, Sofer Z, Bouša D, Varma RS, Gawande MB, Zbořil R (2020) Chem Eng J 382:122469
Corma A, Concepción P, Serna P (2007) Angew Chem Int Ed 46:7266
Kataoka S, Takeuchi Y, Harada A, Takagi T, Takenaka Y, Fukaya N, Yasuda H, Ohmori T, Endo A (2012) Appl Catal A Gen 427:119
Acknowledgements
The authors appreciate partial financial supports from Alzahra University. M.M.H. is also thankful to Iran National Science Foundation (INSF) for the individual given grant.
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Mohammadkhani, L., Heravi, M.M. & Panahi, F. Efficient and heterogeneous transfer hydrogenation of nitroarenes using immobilized palladium nanoparticles on silica–starch substrate (PNP-SSS). Monatsh Chem 153, 623–633 (2022). https://doi.org/10.1007/s00706-022-02932-w
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DOI: https://doi.org/10.1007/s00706-022-02932-w