Abstract
Pharmaceutically active ingredients such as biphenyls and biphenyl diols were synthesized using MIL-101(Cr) catalyst. The Metal Organic Framework, MIL-101(Cr) catalyst was synthesized using the hydrothermal method. Different phases in the as-synthesized MIL-101(Cr) catalyst were characterized using the X-ray diffraction technique. Fourier transform infrared spectroscopy (FTIR) was used to identify various functional groups present in the synthesized material, Field emission-scanning electron microscopy and Transmission electron microscopy were used to study the morphology of the sample. The chemical composition of MIL-101(Cr) was investigated using Energy-dispersive X-ray spectroscopy. Particle size and zeta potential measurements were performed, which provided information about surface charge and stability in the suspension. The catalyst MIL-101(Cr) was used to carry out the Ullmann reaction due to its large surface area, tunable porosity, and easy extraction from the reaction mixture. Biphenyls and biphenyl diols were refluxed in ethanol using MIL-101(Cr) catalyst. This is a very clean and efficient synthetic method for synthesizing biphenyls and biphenyl diols. As synthesized biphenyls and biphenyl diols were characterized by FTIR, 1H and 13C NMR. The retention of catalytic activity up to five cycles, completion of the reaction in an extremely short time, maximum yield, environment friendly and mild reaction conditions are the benefits of our work.
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References
A. Vinu, M. Miyahara, T. Mori, K. Ariga, J. Porous Mater. 13, 379 (2006)
R.S. Salama, S.M. El-Bahy, M.A. Mannaa, Colloids Surf. A Physicochem. Eng. Asp. 628, 127261 (2021)
G. Férey, Chem. Soc. Rev. 37, 191 (2008)
J. Liu, L. Chen, H. Cui, J. Zhang, L. Zhang, C.-Y. Su, Chem. Soc. Rev. 43, 6011 (2014)
H.M. Altass, M. Morad, A.E.R.S. Khder, M.A. Mannaa, R.S. Jassas, A.A. Alsimaree, S.A. Ahmed, R.S. Salama, J. Taiwan Inst. Chem. Eng. 128, 194 (2021)
R. Salama, Delta Univ. Sci. J. 2, 10 (2019)
S.M. El-Dafrawy, R.S. Salama, S.A. El-Hakam, S.E. Samra, J. Mater. Res. Technol. 9, 1998 (2020)
A. Yadav, R.V. Patel, B.G. Vyas, P.K. Labhasetwar, V.K. Shahi, Colloids Surf. A Physicochem. Eng. Asp. 645, 128918 (2022)
L.E. Kreno, K. Leong, O.K. Farha, M. Allendorf, R.P. Van Duyne, J.T. Hupp, Chem. Rev. 112, 1105 (2011)
P. Horcajada, T. Chalati, C. Serre, B. Gillet, C. Sebrie, T. Baati, J.F. Eubank, D. Heurtaux, P. Clayette, C. Kreuz, J.-S. Chang, Y.K. Hwang, V. Marsaud, P.-N. Bories, L. Cynober, S. Gil, G. Férey, P. Couvreur, R. Gref, Nat. Mater. 9, 172 (2009)
P. Horcajada, R. Gref, T. Baati, P.K. Allan, G. Maurin, P. Couvreur, G. Férey, R.E. Morris, C. Serre, Chem. Rev. 112, 1232 (2011)
R.V. Patel, A. Yadav, J. Mol. Struct. 1252, 132128 (2022)
R.S. Salama, M.A. Mannaa, H.M. Altass, A.A. Ibrahim, A.E.R.S. Khder, RSC Adv. 11, 4318 (2021)
R.S. Salama, S.M. Hassan, A.I. Ahmed, W.S.A. El-Yazeed, M.A. Mannaa, RSC Adv. 10, 21115 (2020)
F.T. Alshorifi, D.E. Tobbala, S.M. El-Bahy, M.A. Nassan, R.S. Salama, Catal. Commun. 169, 106479 (2022)
R. Salama, S.A. El-Hakam, S. Samra, S. El-Dafrawy, A. Ibrahim, A. Ahmed, Delta Univ. Sci. J. 6, 266 (2023)
P. Yadav, A. Yadav, P.K. Labhasetwar, Environ. Sci. Pollut. Res. 29, 37204 (2022)
A. Yadav, R.V. Patel, P.K. Labhasetwar, V.K. Shahi, J. Water Process Eng. 43, 102317 (2021)
Y.-G. Sun, G. Xiong, M.-Y. Guo, F. Ding, S.-J. Wang, P.F. Smet, D. Poelman, E.-J. Gao, F. Verpoort, Dalt. Trans. 41, 7670 (2012)
M. Kurmoo, Chem. Soc. Rev. 38, 1353 (2009)
C. Wang, Z. Xie, K.E. Krafft, W. Lin, J. Am. Chem. Soc. 133, 13445 (2011)
S. Bhattacharjee, C. Chen, W.-S. Ahn, RSC Adv. 4, 52500 (2014)
I. Yellapurkar, S. Bhabal, M.M.V. Ramana, K. Jangam, V. Salve, S. Patange, P. More, Res. Chem. Intermed. 47, 2669 (2021)
P. Patil, S. Kadam, D. Patil, P. More, Catal. Commun. 170, 106500 (2022)
P. Patil, S. Kadam, D. Patil, P. More, J. Mol. Liq. 345, 117867 (2022)
R. Athavale, S. Gardi, F. Choudhary, D. Patil, N. Chandan, P. More, Appl. Catal. A Gen. 669, 119505 (2024)
Z.J. Jain, P.S. Gide, R.S. Kankate, Arab. J. Chem. 10, S2051 (2017)
K.C. Nicolaou, C.N.C. Boddy, S. Bräse, N. Winssinger, Angew. Chemie Int. Ed. 38, 2096 (1999)
B. Yuan, Y. Pan, Y. Li, B. Yin, H. Jiang, Angew. Chemie Int. Ed. 49, 4054 (2010)
M. Bahadori, S. Tangestaninejad, M. Moghadam, V. Mirkhani, A. Mechler, I. Mohammadpoor-Baltork, F. Zadehahmadi, Microporous Mesoporous Mater. 253, 102 (2017)
F. Carson, V. Pascanu, A. Bermejo Gómez, Y. Zhang, A.E. Platero-Prats, X. Zou, B. Martín-Matute, Chem.—A Eur. J. 21, 10896 (2015)
S. Sadeghi, M. Jafarzadeh, A. Reza Abbasi, K. Daasbjerg, New J. Chem. 41, 12014 (2017)
V. Pascanu, Q. Yao, A. Bermejo Gómez, M. Gustafsson, Y. Yun, W. Wan, L. Samain, X. Zou, B. Martín-Matute, Chemistry 19, 17483 (2013)
Y. Hayashi, N. Obata, M. Tamaru, S. Yamaguchi, Y. Matsuo, A. Saeki, S. Seki, Y. Kureishi, S. Saito, S. Yamaguchi, H. Shinokubo, Org. Lett. 14, 866 (2012)
G. Yang, S.-J. Park, Materials (Basel) 12, 1177 (2019)
P. Hou, G. Xing, D. Han, Y. Zhao, G. Zhang, H. Wang, C. Zhao, C. Yu, J. Porous Mater. 26, 1607 (2019)
X. Zheng, J. Wang, Int. J. Anal. Chem. 2019, 2547280 (2019)
H. Su, J. Lv, L. Yang, L. Feng, Y. Liu, Z. Du, L. Zhang, RSC Adv. 10, 2198 (2020)
A. Jarrah, S. Farhadi, Acta Chim. Slov. 66, 85 (2019)
X. Huang, Q. Hu, L. Gao, Q. Hao, P. Wang, D. Qin, RSC Adv. 8, 27623 (2018)
R. Karimi Alavijeh, K. Akhbari, Inorg. Chem. 59, 3570 (2020)
Acknowledgements
JT, MG and PM are thankful to the management, Secretary Dr. B.B.Sharma and Principal Prof. (Dr.) Preeta Nilesh of K.E.T’S,V.G.Vaze College Autonomous for the laboratory facilities.
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JT and MG: Synthesis of catalyst, biphenyl and biphenyl diol derivatives; AY and KW: Characterization and interpretation of derivatives; PM: Conceptualization of idea, combine all the results and writing the manuscript.
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Tripathi, J., Gupta, M., Yadav, A. et al. Metal–organic framework MIL-101(Cr): an efficient catalyst for the synthesis of biphenyls and biphenyl diols. Res Chem Intermed 50, 1645–1660 (2024). https://doi.org/10.1007/s11164-024-05240-6
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DOI: https://doi.org/10.1007/s11164-024-05240-6