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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Research Article

Celecoxib Catalyzed the Coupling Reaction of Epoxide and CO2

Author(s): Ling Wu, Xiaocheng Xia, Wenying An, Wenshan Cui, Yue Liu, Wei Lv and Fengtian Wu*

Volume 21, Issue 7, 2024

Published on: 24 January, 2024

Page: [611 - 619] Pages: 9

DOI: 10.2174/0115701786276731231206113215

Price: $65

Abstract

In this study, high yields of various cyclic carbonates are obtained by employing the drug celecoxib to promote the coupling reaction of CO2 and epoxide using tetrabutylammonium bromide. This strategy enables the synthesis of benzoic acid, phenylpropiolic acid, and 2, 4- quinazolinedione. In addition, the model reaction mechanism is proposed.

Graphical Abstract

[1]
Lu, X.B.; Darensbourg, D. J. Chem. Soc. Rev., 2012, 41(4), 1462-1484.
[http://dx.doi.org/10.1039/C1CS15142H] [PMID: 21858339]
[2]
Kenar, J.A.; Tevis, I.D. Eur. J. Lipid Sci. Technol., 2005, 107(2), 135-137.
[http://dx.doi.org/10.1002/ejlt.200401110]
[3]
Burk, R.M.; Roof, M.B. Tetrahedron Lett., 2010, 24(22), 101-109.
[4]
Wu, F.; Lin, Y. Appl. Organomet. Chem., 2020, 34(3), e5427.
[http://dx.doi.org/10.1002/aoc.5427]
[5]
Fiorani, G.; Guo, W.; Kleij, A.W. Green Chem., 2015, 17(3), 1375-1389.
[http://dx.doi.org/10.1039/C4GC01959H]
[6]
Liu, F.; Gu, Y.; Xin, H.; Zhao, P.; Gao, J.; Liu, M. ACS Sustain. Chem.& Eng., 2019, 7(19), 16674-16681.
[http://dx.doi.org/10.1021/acssuschemeng.9b04090]
[7]
Yan, T.; Liu, H.; Zeng, Z. X.; Pan, W. G. 2023, 68, 102355.
[8]
Wang, Z.; Wang, Y.; Xie, Q.; Fan, Z.; Shen, Y. New J. Chem., 2021, 45(21), 9403-9408.
[http://dx.doi.org/10.1039/D1NJ01285A]
[9]
Rostami, A.; Ebrahimi, A.; Al-Jassasi, M.; Mirzaei, S.; Al-Harrasi, A. Green Chem., 2022, 24(23), 9069-9083.
[http://dx.doi.org/10.1039/D2GC02146C]
[10]
Guo, L.; Lamb, K.J.; North, M. Green Chem., 2021, 23(1), 77-118.
[http://dx.doi.org/10.1039/D0GC03465G]
[11]
Debruyne, M.; Van Speybroeck, V.; Van Der Voort, P.; Stevens, C.V. Green Chem., 2021, 23(19), 7361-7434.
[http://dx.doi.org/10.1039/D1GC02319E]
[12]
Lyu, H.; Wang, X.; Sun, W.; Xu, E.; She, Y.; Liu, A.; Gao, D.; Hu, M.; Guo, J.; Hu, K.; Cheng, J.; Long, Z.; Liu, Y.; Zhang, P. Green Chem., 2023, 25(9), 3592-3605.
[http://dx.doi.org/10.1039/D3GC00009E]
[13]
Dolai, M.; Biswas, S.; Moreno-Pineda, E.; Wernsdorfer, W.; Ali, M.; Alshgari, R.A.; Wabaidur, S.M.; Ghosh, A. Cryst. Growth Des., 2023, 23(2), 801-810.
[http://dx.doi.org/10.1021/acs.cgd.2c01026]
[14]
Mesías-Salazar, Á.; Martínez, J.; Rojas, R.S.; Carrillo-Hermosilla, F.; Ramos, A.; Fernández-Galán, R.; Antiñolo, A. Catal. Sci. Technol., 2019, 9(15), 3879-3886.
[http://dx.doi.org/10.1039/C9CY00667B]
[15]
Zhang, Z.; Fan, F.; Xing, H.; Yang, Q.; Bao, Z.; Ren, Q. ACS Sustain. Chem.& Eng., 2017, 5(4), 2841-2846.
[http://dx.doi.org/10.1021/acssuschemeng.7b00513]
[16]
Li, W.; Cheng, W.; Yang, X.; Su, Q.; Dong, L.; Zhang, P.; Yi, Y.; Li, B.; Zhang, S. Chin. J. Chem., 2018, 36(4), 293-298.
[http://dx.doi.org/10.1002/cjoc.201700747]
[17]
Arayachukiat, S.; Kongtes, C.; Barthel, A.; Vummaleti, S.V.C.; Poater, A.; Wannakao, S.; Cavallo, L.; D’Elia, V. ACS Sustain. Chem.& Eng., 2017, 5(8), 6392-6397.
[http://dx.doi.org/10.1021/acssuschemeng.7b01650]
[18]
Li, Q.; Chang, H.; Li, R.; Wang, H.; Liu, J.; Liu, S.; Qiao, C.; Lin, T. Molecular Catalysis, 2019, 469, 111-117.
[http://dx.doi.org/10.1016/j.mcat.2019.03.012]
[19]
Castro-Osma, J.A.; Martínez, J.; de la Cruz-Martínez, F.; Caballero, M.P.; Fernández-Baeza, J.; Rodríguez-López, J.; Otero, A.; Lara-Sánchez, A. Tejeda. J. Catal. Sci. Technol., 2018, 8(7), 1981-1987.
[http://dx.doi.org/10.1039/C8CY00381E]
[20]
Pawar, A.A.; Kim, H.J. CO2 Util., 2019, 33, 500-512.https://www.sciencedirect.com/science/article/pii/S221298201930383X
[21]
Mujmule, R.B.; Rao, M.P.R.; Rathod, P.V.; Deonikar, V.G.; Chaugule, A.A.; Kim, H.J. CO2 Util., 2019, 33, 284-291.https://www.sciencedirect.com/science/article/pii/S221298201930335X
[22]
Liu, N.; Xie, Y.F.; Wang, C.; Li, S.J.; Wei, D.; Li, M.; Dai, B. ACS Catal., 2018, 8(11), 9945-9957.
[http://dx.doi.org/10.1021/acscatal.8b01925]
[23]
Guo, Y.; Jiang, D.; Mai, Z.; Chen, Y.; Li, T.; Gao, G. Clin. Rheumatol., 2023, 42(6), 1585-1592.
[http://dx.doi.org/10.1007/s10067-023-06541-8] [PMID: 36800138]
[24]
Yang, Z.Z.; Zhao, Y.; Ji, G.; Zhang, H.; Yu, B.; Gao, X.; Liu, Z. Green Chem., 2014, 16(8), 3724-3728.
[http://dx.doi.org/10.1039/C4GC00730A]
[25]
Pearson, D.M.; Conley, N.R.; Waymouth, R.M. Adv. Synth. Catal., 2011, 353(16), 3007-3013.
[http://dx.doi.org/10.1002/adsc.201100240]
[26]
Amaral, A.J.R.; Coelho, J.F.J.; Serra, A.C. Tetrahedron Lett., 2013, 54(40), 5518-5522.
[http://dx.doi.org/10.1016/j.tetlet.2013.07.152]
[27]
Poletti, L.; Rovegno, C.; Di Carmine, G.; Vacchi, F.; Ragno, D.; Brandolese, A.; Massi, A.; Dambruoso, P. Molecules, 2023, 28(4), 1530.
[http://dx.doi.org/10.3390/molecules28041530] [PMID: 36838518]
[28]
Sharma, R.; Bansal, A.; Ramachandran, C.N.; Mohanty, P.C. Commun., 2019, 55, 11607-11610.
[29]
Xu, N.; Peng, X.; Luo, C.; Huang, L.; Wang, C.; Chen, Z. Li. J. Adv. Synth. Catal., 2023, 365(2), 142-147.
[http://dx.doi.org/10.1002/adsc.202201076]
[30]
Xiong, W.; Wang, Y.; Yang, X.; Liu, W.H. Org. Lett., 2023, 25(17), 2948-2952.
[http://dx.doi.org/10.1021/acs.orglett.3c00354] [PMID: 36853098]
[31]
Zhang, L.; Chen, Q.; Li, L.; Ma, N.; Tian, J.; Sun, H.; Xu, Q.; Yang, Y.; Li, C. Org. Lett., 2023, 25(14), 2471-2475.
[http://dx.doi.org/10.1021/acs.orglett.3c00614] [PMID: 37017368]

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