Abstract
Ni0 nanoparticles were immobilized on acid-activated montmorillonite (Ni0-Mont) by anchoring Ni(OAc)2·4H2O on modified micro/mesoporous montmorillonite followed by reduction with ethylene glycol. The prepared clay composite system was then characterized using Fourier-transform infrared (FT-IR) spectroscopy, scanning electron microscopy (SEM), energy-dispersive X-ray (EDX) spectroscopy, X-ray diffraction (XRD) analysis, and Brunauer–Emmett–Teller (BET) analysis. SEM analysis revealed perfect dispersion of metallic nickel nanoparticles with size distribution of 6‒41 nm on the clay matrix. Micro/mesoporous montmorillonite was prepared by activation of Na+-montmorillonite with HCl (4 M) under controlled conditions. The catalytic activity of the prepared Ni0-Mont clay was studied in one-pot microwave-assisted synthesis of biscoumarins and bisdimedones via Knoevenagel reaction of aromatic aldehydes with 4-hydroxycoumarin or dimedone in solvent-free conditions. All reactions were carried out at room temperature within 5‒15 min (for biscoumarins) and 5–20 min (for bisdimedones) to afford the products in high to excellent yield. The reusability of the Ni0-Mont catalyst was also investigated in seven consecutive cycles, without significant loss of catalytic activity.
This is a preview of subscription content, access via your institution.











References
X. Xie, Y. Li, Z.Q. Liu, M. Haruta, W. Shen, Nature 458, 746 (2009)
C.N. Ramachandra Rao, G.U. Kulkarni, P.J. Thomas, P.P. Edwards, Chem. Soc. Rev. 29, 27 (2000)
E. Formo, E. Lee, D. Campbell, Y. Xia, Nano Lett. 8, 668 (2008)
N. Zheng, G.D. Stucky, J. Am. Chem. Soc. 128, 14278 (2006)
Z. Huang, F. Cui, H. Kang, J. Chen, X. Zhang, C. Xia, Chem. Mater. 20, 5090 (2008)
B. Suresh Kumar, A. Dhakshinamoorthy, K. Pitchumani, Catal. Sci. Technol. 4, 2378 (2014)
S. Bai, X. Shen, G. Zhu, M. Li, H. Xi, K. Chen, ACS Appl. Mater. Interfaces 4, 2378 (2012)
F. Davar, Z. Fereshteh, M. Salavati-Niasari, J. Alloys Compd. 476, 797 (2009)
L.K. Yeung, R.M. Crooks, Nano Lett. 1, 14 (2001)
F.S. Han, Chem. Soc. Rev. 42, 5270 (2013)
L. Wu, J. Ling, Z.Q. Wu, Adv. Synth. Catal. 353, 1452 (2011)
Y.L. Zhao, Y. Li, S.M. Li, Y.G. Zhou, F.Y. Sun, L.X. Gao, F.S. Han, Adv. Synth. Catal. 353, 1543 (2011)
F. Alonso, P. Riente, M. Yus, Synlett 9, 1289 (2008)
S.Z. Tasker, A.C. Gutierrez, T.F. Jamison, Angew. Chem. Int. Ed. 53, 1858 (2014)
W. Zhang, H. Qi, L. Li, X. Wang, J. Chen, K. Peng, Z. Wang, Green Chem. 11, 1194 (2009)
C. Zheng, S.S. Stahl, Chem. Commun. 51, 12771 (2015)
S.B. Sapkal, K.F. Shelke, B.B. Shingate, M.S. Shingare, Tetrahedron Lett. 50, 1754 (2009)
J.M. Khurana, K.Vij Sneha, Synth. Commun. 42, 2606 (2012)
M. Saha, B. Das, A. Kumar Pal, C. R. Chim. 16, 1079 (2013)
T. Tsukatani, H. Fujihara, Langmuir 21, 12093 (2005)
D. Dutta, B.J. Borah, L. Saikia, M.G. Pathak, P. Sengupta, D.K. Dutta, Appl. Clay Sci. 53, 650 (2011)
J.D. Aiken, R.G. Finke, J. Am. Chem. Soc. 121, 8803 (1999)
M. Tamura, H. Fujihara, J. Am. Chem. Soc. 125, 15742 (2003)
V.K. Sharma, R.A. Yngard, Y. Lin, Adv. Colloid Interface Sci. 145, 83 (2009)
N. Mahata, A.F. Cunha, J.J.M. Orfao, J.L. Figueiredo, Appl. Catal. 351, 204 (2008)
F. Schröder, D. Esken, M. Cokoja, M.W. van den Berg, O.I. Lebedev, G. Van Tendeloo, B. Walaszek, G. Buntkowsky, H.H. Limbach, B. Chaudret, R.A. Fischer, J. Am. Chem. Soc. 130, 6119 (2008)
D.H. Chen, C.H. Hsieh, J. Mater. Chem. 12, 2412 (2002)
J.M. Campelo, T.D. Conesa, M.J. Gracia, M.J. Jurado, R. Luque, J.M. Marinas, A.A. Romero, Green Chem. 10, 853 (2008)
S. Pande, A. Saha, S. Jana, S. Sarkar, M. Basu, M. Pradhan, A.K. Sinha, S. Saha, A. Pal, T. Pal, Org. Lett. 10, 5179 (2008)
M.L. Kantam, R. Chakravarti, U. Pal, B. Sreedhar, S. Bhargava, Synfacts 7, 767 (2008)
Z. Király, I. Dékány, Á. Mastalir, M. Bartók, J. Catal. 161, 401 (1996)
P. Sharma, S.K. Bhorodwaj, D.K. Dutta, in Journal of Scientific Conference Proceedings (American Scientific Publishers, 2009), p. 40
A. Gil, S.A. Korili, R. Trujillano, M.A. Vicente, Pillared Clays and Related Catalysts (Springer, Heidelberg, 2010)
O.S. Ahmed, D.K. Dutta, Langmuir 19, 5540 (2003)
P.B. Malla, P. Ravindranathan, S. Komarneni, R. Roy, Nature 351, 555 (1991)
R.S. Varma, Tetrahedron 58, 1235 (2002)
I. Manolov, C. Maichle-Moessmer, N. Danchev, Eur. J. Med. Chem. 41, 882 (2006)
E. Adami, U.E. Marazzi, C. Turba, Arch. Ital. Sci. Farmacol. 9, 61 (1959)
Z.H. Chohan, A.U. Shaikh, A. Rauf, C.T. Supuran, J. Enzyme Inhib. Med. Chem. 21, 741 (2006)
N. Hamdi, M.C. Puerta, P. Valerga, Eur. J. Med. Chem. 43, 2541 (2008)
A.C. Luchini, P. Rodrigues-Orsi, S.H. Cestari, L.N. Seito, A. Witaicenis, C.H. Pellizzon, L.C. Di Stasi, Biol. Pharm. Bull. 31, 1343 (2008)
D.H. Mahajan, C. Pannecouque, E. De Clercq, K.H. Chikhalia, Arch. Pharm. (Weinheim) 342, 281 (2009)
M.A. Velasco-Velázquez, J. Agramonte-Hevia, D. Barrera, A. Jiménez-Orozco, M.A.J. Garcı́a-Mondragón, N. Mendoza-Patiño, A. Landa, J. Mandoki, Cancer Lett. 198, 179 (2003)
D. Završnik, S. Muratović, D. Makuc, J. Plavec, M. Cetina, A. Nagl, E.D. Clercq, J. Balzarini, M. Mintas, Molecules 16, 6023 (2011)
M. Gersch, J. Kreuzer, S.A. Sieber, Nat. Prod. Rep. 29, 659 (2012)
K. Petnapapun, W. Chavasiri, P. Sompornpisut, Sci. World J. 2013, 178649 (2013)
M. Kidwai, V. Bansal, P. Mothsra, S. Saxena, R.K. Somvanshi, S. Dey, T.P. Singh, J. Mol. Catal. A Chem. 268, 76 (2007)
K.H. Khan, S. Iqbal, M.A. Lodhi, G.M. Maharvi, Z. Ullah, M.I. Choudhary, A.U. Rahman, S. Perveen, Bioorgan. Med. Chem. 12, 1963 (2004)
H. Hagiwara, N. Fujimoto, T. Suzuki, M. Ando, Heterocycles 53, 549 (2000)
A. Shamsaddini, E. Sheikhhosseini, Int. J. Org. Chem. 4, 135 (2014)
H. Mehrabi, H. Abusaidi, J. Iran. Chem. Soc. 7, 890 (2010)
Z.N. Siddiqui, T.N. Mohammed Musthafa, S. Praveen, F. Farooq, Med. Chem. Res. 20, 1438 (2011)
J.M. Khurana, S. Kumar, Tetrahedron Lett. 50, 4125 (2009)
A. Tzani, A. Douka, A. Papadopoulos, E.A. Pavlatou, E. Voutsas, A. Detsi, ACS Sustain. Chem. Eng. 1, 1180 (2013)
R. Karimian, F. Piri, A.A. Safari, S.J. Davarpanah, J. Nanostruct. Chem. 3, 52 (2013)
A.M. Al-Majid, M. Shahidul Islam, A. Barakat, N.J. Al-Qahtani, S. Yousuf, M. Iqbal Choudhary, Arab. J. Chem. 10, 185 (2017)
D. Arora, J. Dwivedi, S. Kumar, D. Kishore, Synth. Commun. 48, 115 (2018)
A.G. Banerjee, L.P. Kothapalli, P.A. Sharma, A.B. Thomas, R.K. Nanda, S.K. Shrivastava, V.V. Khatanglekar, Arab. J. Chem. 9, S480 (2016)
S.A. Hilderbrand, R. Weissleder, Tetrahedron Lett. 48, 4383 (2007)
G. Pohlers, J. Scaiano, R. Sinta, Chem. Mater. 9, 3222 (1997)
C.G. Knight, T. Stephens, Biochem. J. 258, 683 (1989)
S. Hatakeyama, N. Ochi, H. Numata, S. Takano, J. Chem. Soc. Chem. Commun. 17, 1202 (1988)
M.A. Mekewi, A.S. Darwish, M.S. Amin, G. Eshaq, H.A. Bourazan, Egypt. J. Petrol. 25, 269 (2016)
R. Das, S.S. Nath, R. Bhattacharjee, J. Fluoresc. 21, 1165 (2011)
B. Bagchi, S. Kar, S.K. Dey, S. Bhandary, D. Roy, T.K. Mukhopadhyay, S. Das, P. Nandy, Colloid Surf. B Biointerfaces 108, 358 (2013)
B. Sahin, T. Kaya, Appl. Surf. Sci. 362, 532 (2016)
E. Şennik, S. Kerli, Ü. Alver, Z.Z. Öztürk, Sens. Actuators B 216, 49 (2015)
S.K. Bhorodwaj, D.K. Dutta, Appl. Catal. A 378, 221 (2010)
L. Saikia, D. Dutta, D.K. Dutta, Catal. Commun. 19, 1 (2012)
A. Dhakshinamoorthy, K. Pitchumani, Tetrahedron Lett. 49, 1818 (2008)
S. Brunauer, L.S. Deming, W.E. Deming, E. Teller, J. Am. Chem. Soc. 62, 1723 (1940)
G.B.B. Varadwaj, S. Rana, K. Parida, Chem. Eng. J. 215–216, 849 (2013)
P.K. Saikia, P.P. Sarmah, B.J. Borah, L. Saikia, K. Saikia, D. Kumar Dutta, Green Chem. 18, 2843 (2016)
J. Ji, P. Zeng, S. Ji, W. Yang, H. Liu, Y. Li, Catal. Today 158, 305 (2010)
S.K. Bhorodwaj, M.G. Pathak, D.K. Dutta, Catal. Lett. 133, 185 (2009)
S. Qadir, A. Ahmad Dar, K. Zaman Khan, Synth. Commun. 38, 3490 (2008)
N. Tavakoli-Hoseini, M.M. Heravi, F.F. Bamoharram, A. Davoodnia, M. Ghassemzadeh, J. Mol. Liq. 163, 122 (2011)
J.M. Khurana, K. Vij, J. Chem. Sci. 124, 907 (2012)
B. Karmakar, A. Nayak, J. Banerji, Tetrahedron Lett. 53, 4343 (2012)
B. Pawar, V. Shinde, A. Chaskar, Green Sustain. Chem. 3, 56 (2013)
K. Niknam, A. Jamali, Chin. J. Catal. 33, 1840 (2012)
I. Manolov, C. Maichle-Moessmer, I. Nicolova, N. Danchev, Arch. Pharm. 339, 319 (2006)
W. Li, Y. Wang, Z. Wang, L. Dai, Y. Wang, Catal. Lett. 141, 1651 (2011)
Acknowledgements
The authors gratefully acknowledged financial support of this work by the research council of Urmia University.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Rahmani, S., Zeynizadeh, B. Ni0 NPs anchored on acid-activated montmorillonite (Ni0-Mont) as a highly efficient and reusable nanocatalyst for synthesis of biscoumarins and bisdimedones. Res Chem Intermed 45, 1227–1248 (2019). https://doi.org/10.1007/s11164-018-3671-y
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-018-3671-y