Generic placeholder image

Letters in Organic Chemistry

Author(s): Haiyan Zhu, Chen Yang and Zheng-Chao Duan*

DOI: 10.2174/1570178620666230221101758

DownloadDownload PDF Flyer Cite As
The Preparation of Zr-containing Coordination Polymer as an Efficient Catalyst for Alkylation of Amines and Alcohols

Page: [770 - 778] Pages: 9

  • * (Excluding Mailing and Handling)

Abstract

A coordination polymer Zr-CIA was developed and employed as a stable and effective catalyst for the alkylation of amines with alcohols or benzyl amines. The Zr-CIA as a new coordination polymer was prepared from 1-(carboxymethyl)-1H-indole-3-carboxylic acid and ZrCl4 through a simple and effective solvothermal method and characterized by scanning electron microscopy (SEM), transmission electron microscopy (TEM), powder X-ray diffraction (XRD), fourier transform infrared (FT-IR), nitrogen adsorption-desorption and X-ray photoelectronic spectroscopy (XPS). The polymer exhibited not only high catalytic activity for the alkylation reaction, but also good reusability in more than five cycles. Meanwhile, mechanistic investigations were carried out to study these reactions.

Graphical Abstract

[1]
Niu, F.; Tu, W.; Lu, X.; Chi, H.; Zhu, H.; Zhu, X.; Wang, L.; Xiong, Y.; Yao, Y.; Zhou, Y.; Zou, Z. ACS Catal., 2022, 12(8), 4481-4490.
[http://dx.doi.org/10.1021/acscatal.2c00433]
[2]
Jin, M.Y.; Zhou, Y.; Xiao, D.; You, Y.; Zhen, Q.; Tao, G.; Yu, P.; Xing, X. Angew. Chem. Int. Ed., 2022, 61(3)e202112993
[http://dx.doi.org/10.1002/anie.202112993] [PMID: 34626073]
[3]
Maji, M.; Borthakur, I.; Guria, S.; Singha, S.; Kundu, S. J. Catal., 2021, 402, 37-51.
[http://dx.doi.org/10.1016/j.jcat.2021.08.010]
[4]
Ma, Z.; Zhou, B.; Li, X.; Kadam, R.G.; Gawande, M.B.; Petr, M.; Zbořil, R.; Beller, M.; Jagadeesh, R.V. Chem. Sci. (Camb.), 2021, 13(1), 111-117.
[http://dx.doi.org/10.1039/D1SC05913K]
[5]
Yang, Q.; Zhang, Y.; Zeng, W.; Duan, Z.C.; Sang, X.; Wang, D. Green Chem., 2019, 21(20), 5683-5690.
[http://dx.doi.org/10.1039/C9GC02409C]
[6]
Reed-Berendt, B.G.; Latham, D.E.; Dambatta, M.B.; Morrill, L.C. ACS Cent. Sci., 2021, 7(4), 570-585.
[http://dx.doi.org/10.1021/acscentsci.1c00125] [PMID: 34056087]
[7]
Alig, L.; Fritz, M.; Schneider, S. Chem. Rev., 2019, 119(4), 2681-2751.
[http://dx.doi.org/10.1021/acs.chemrev.8b00555] [PMID: 30596420]
[8]
Irrgang, T.; Kempe, R. Chem. Rev., 2019, 119(4), 2524-2549.
[http://dx.doi.org/10.1021/acs.chemrev.8b00306] [PMID: 30457320]
[9]
Wei, D.; Darcel, C. Chem. Rev., 2019, 119(4), 2550-2610.
[http://dx.doi.org/10.1021/acs.chemrev.8b00372] [PMID: 30548065]
[10]
Corma, A.; Navas, J.; Sabater, M. J. Chem. Rev., 2018, 118(4), 1410-1459.
[http://dx.doi.org/10.1021/acs.chemrev.7b00340] [PMID: 29319294]
[11]
Yang, Q.; Wang, Q. Yu. Z. Chem. Soc. Rev., 2015, 44(8), 2305-2329.
[http://dx.doi.org/10.1039/C4CS00496E] [PMID: 25661436]
[12]
Nandakumar, A.; Midya, S.P.; Landge, V.G.; Balaraman, E. Angew. Chem. Int. Ed., 2015, 54(38), 11022-11034.
[http://dx.doi.org/10.1002/anie.201503247] [PMID: 26269420]
[13]
Hao, S.; Yang, J.; Liu, P.; Xu, J.; Yang, C.; Li, F. Org. Lett., 2021, 23(7), 2553-2558.
[http://dx.doi.org/10.1021/acs.orglett.1c00475] [PMID: 33729807]
[14]
Li, C.; Wan, K.; Guo, F.; Wu, Q.; Yuan, M.; Li, R.; Fu, H.; Zheng, X.; Chen, H. J. Org. Chem., 2019, 84(4), 2158-2168.
[http://dx.doi.org/10.1021/acs.joc.8b03137] [PMID: 30676029]
[15]
Chelucci, G. Coord. Chem. Rev., 2017, 331, 1-36.
[http://dx.doi.org/10.1016/j.ccr.2016.10.002]
[16]
Huang, F.; Liu, Z. Yu. Z. Angew. Chem. Int. Ed., 2016, 55(3), 862-875.
[http://dx.doi.org/10.1002/anie.201507521] [PMID: 26639633]
[17]
Chen, B.; Wang, L.; Gao, S. ACS Catal., 2015, 5(10), 5851-5876.
[http://dx.doi.org/10.1021/acscatal.5b01479]
[18]
Wang, D.; Xia, X.; Hu, W.; Yang, Y.; Li, J. Youji Huaxue, 2022, 42, 190.
[http://dx.doi.org/10.6023/cjoc202107018]
[19]
Haldar, J.; An, D.; Álvarez de Cienfuegos, L.; Chen, J.; Klibanov, A.M. Proc. Natl. Acad. Sci. USA, 2006, 103(47), 17667-17671.
[http://dx.doi.org/10.1073/pnas.0608803103] [PMID: 17101983]
[20]
Frueh, J.; Gai, M.; Yang, Z.; He, Q. J. Nanosci. Nanotechnol., 2014, 14(6), 4341-4350.
[http://dx.doi.org/10.1166/jnn.2014.8226] [PMID: 24738394]
[21]
Zhang, J. Wang. J. Angew. Chem. Int. Ed., 2018, 57(2), 465-469.
[http://dx.doi.org/10.1002/anie.201711126] [PMID: 29143422]
[22]
Wong, C.M.; McBurney, R.T.; Binding, S.C.; Peterson, M.B.; Gonçales, V.R.; Gooding, J.J.; Messerle, B.A. Green Chem., 2017, 19(13), 3142-3151.
[http://dx.doi.org/10.1039/C7GC01007A]
[23]
Genç, S.; Arslan, B.; Gülcemal, S.; Günnaz, S.; Çetinkaya, B.; Gülcemal, D. J. Org. Chem., 2019, 84(10), 6286-6297.
[http://dx.doi.org/10.1021/acs.joc.9b00632] [PMID: 30986066]
[24]
Hall, C.J.J.; Goundry, W.R.F.; Donohoe, T.J. Angew. Chem. Int. Ed., 2021, 60(13), 6981-6985.
[http://dx.doi.org/10.1002/anie.202100922] [PMID: 33561302]
[25]
Liu, P.; Yang, J.; Ai, Y.; Hao, S.; Chen, X.; Li, F. J. Catal., 2021, 396, 281-290.
[http://dx.doi.org/10.1016/j.jcat.2021.02.030]
[26]
Lu, Z.; Zheng, Q.; Yang, S.; Qian, C.; Shen, Y.; Tu, T. ACS Catal., 2021, 11(17), 10796-10801.
[http://dx.doi.org/10.1021/acscatal.1c02700]
[27]
Liu, T.; Wang, L.; Wu, K.; Yu, Z. ACS Catal., 2018, 8(8), 7201-7207.
[http://dx.doi.org/10.1021/acscatal.8b01960]
[28]
Li, J.; Liu, H.; Zhu, H.; Yao, W.; Wang, D. ChemCatChem, 2021, 13(22), 4751-4758.
[http://dx.doi.org/10.1002/cctc.202101168]
[29]
Zhu, G.; Duan, Z.C.; Zhu, H.; Ye, D.; Wang, D. Chin. Chem. Lett., 2022, 33(1), 266-270.
[http://dx.doi.org/10.1016/j.cclet.2021.06.060]
[30]
Wang, D.; Ge, B.; Zhang, B.; Liu, H.; Li, J. Youji Huaxue, 2022, 42, 619.
[http://dx.doi.org/10.6023/cjoc202108026]
[31]
Li, J.; Yu, M.; Duan, Z.C.; Zhu, H.; Yao, W.; Wang, D. Mater. Chem. Front., 2021, 5(21), 7861-7872.
[http://dx.doi.org/10.1039/D1QM00792K]
[32]
Li, J.; Mao, A.; Yao, W.; Zhu, H.; Wang, D. Green Chem., 2022, 24(6), 2602-2612.
[http://dx.doi.org/10.1039/D2GC00190J]
[33]
Patel, N.B.; Vala, N.; Shukla, A.; Neogi, S.; Mishra, M.K. Catal. Commun., 2020, 144106085
[http://dx.doi.org/10.1016/j.catcom.2020.106085]
[34]
Lu, G.P.; Shan, H.; Lin, Y.; Zhang, K.; Zhou, B.; Zhong, Q.; Wang, P. J. Mater. Chem. A Mater. Energy Sustain., 2021, 9(44), 25128-25135.
[http://dx.doi.org/10.1039/D1TA07673F]
[35]
Tian, A.Q.; Luo, X.H.; Ren, Z.L.; Zhao, J.; Wang, L. New J. Chem., 2021, 45(21), 9614-9620.
[http://dx.doi.org/10.1039/D1NJ00861G]
[36]
Bohigues, B.; Rojas-Buzo, S.; Moliner, M.; Corma, A. ACS Sustain. Chem.& Eng., 2021, 9(47), 15793-15806.
[http://dx.doi.org/10.1021/acssuschemeng.1c04903] [PMID: 35663357]
[37]
Wu, P.; Lu, G.; Cai, C. Green Chem., 2021, 23(1), 396-404.
[http://dx.doi.org/10.1039/D0GC03725G]
[38]
Hu, W.; Zhang, Y.; Zhu, H.; Ye, D.; Wang, D. Green Chem., 2019, 21(19), 5345-5351.
[http://dx.doi.org/10.1039/C9GC02086A]
[39]
Luo, X.; Tian, A.; Ren, Z.; Kong, H.; Wang, L. Catal. Lett., 2022, 152(12), 3704-3715.
[http://dx.doi.org/10.1007/s10562-022-03929-0]
[40]
Luo, X.; Tian, A.; Pei, M.; Yan, J.; Liu, X.; Wang, L. Chemistry, 2022, 28(3)e202103361
[http://dx.doi.org/10.1002/chem.202103361] [PMID: 34841580]
[41]
Liu, J.; Liu, N.; Yang, Q.; Wang, L. Org. Chem. Front., 2021, 8(19), 5296-5302.
[http://dx.doi.org/10.1039/D1QO00777G]
[42]
Spokoyny, A.M.; Kim, D.; Sumrein, A.; Mirkin, C.A. Chem. Soc. Rev., 2009, 38(5), 1218-1227.
[http://dx.doi.org/10.1039/b807085g] [PMID: 19384433]
[43]
Tao, R.; Yang, Y.; Zhu, H.; Hu, X.; Wang, D. Green Chem., 2020, 22(23), 8452-8461.
[http://dx.doi.org/10.1039/D0GC02341H]
[44]
Elsaidi, S.K.; Mohamed, M.H.; Banerjee, D.; Thallapally, P.K. Coord. Chem. Rev., 2018, 358, 125-152.
[http://dx.doi.org/10.1016/j.ccr.2017.11.022]
[45]
Ghosh, S.; Hossain, M.S.; Chatterjee, S.; Rahaman, S.A.; Bandyopadhyay, S. ACS Appl. Mater. Interfaces, 2020, 12(47), 52983-52991.
[http://dx.doi.org/10.1021/acsami.0c17513] [PMID: 33185437]
[46]
Jing, Y.; Yoshida, Y.; Huang, P.; Kitagawa, H. Angew. Chem. Int. Ed., 2022, 61(14)e202117417
[http://dx.doi.org/10.1002/anie.202117417] [PMID: 35112452]
[47]
Michaels, H.; Golomb, M.J.; Kim, B.J.; Edvinsson, T.; Cucinotta, F.; Waddell, P.G.; Probert, M.R.; Konezny, S.J.; Boschloo, G.; Walsh, A.; Freitag, M. J. Mater. Chem. A Mater. Energy Sustain., 2022, 10(17), 9582-9591.
[http://dx.doi.org/10.1039/D2TA00267A]
[48]
Fu, P.Y.; Li, B.N.; Zhang, Q.S.; Mo, J.T.; Wang, S.C.; Pan, M.; Su, C.Y. J. Am. Chem. Soc., 2022, 144(6), 2726-2734.
[http://dx.doi.org/10.1021/jacs.1c11874] [PMID: 35001613]
[49]
Thoonen, S.; Tay, H.M.; Hua, C. Chem. Commun. (Camb.), 2022, 58(28), 4512-4515.
[http://dx.doi.org/10.1039/D1CC06872E] [PMID: 35302117]
[50]
Hu, X.; Zhu, H.; Sang, X.; Wang, D. Adv. Synth. Catal., 2018, 360(22), 4293-4300.
[http://dx.doi.org/10.1002/adsc.201800875]
[51]
Sang, X.; Hu, X.; Tao, R.; Zhang, Y.; Zhu, H.; Wang, D. ChemPlusChem, 2020, 85(1), 123-129.
[http://dx.doi.org/10.1002/cplu.201900349]
[52]
Yuan, S.; Chen, Y.P.; Qin, J.S.; Lu, W.; Zou, L.; Zhang, Q.; Wang, X.; Sun, X.; Zhou, H.C. J. Am. Chem. Soc., 2016, 138(28), 8912-8919.
[http://dx.doi.org/10.1021/jacs.6b04501] [PMID: 27345035]
[53]
Song, J.; Wu, L.; Zhou, B.; Zhou, H.; Fan, H.; Yang, Y.; Meng, Q.; Han, B. Green Chem., 2015, 17(3), 1626-1632.
[http://dx.doi.org/10.1039/C4GC02104E]
[54]
Sha, Y.; Xiao, Z.; Zhou, H.; Yang, K.; Song, Y.; Li, N.; He, R.; Zhi, K.; Liu, Q. Green Chem., 2017, 19(20), 4829-4837.
[http://dx.doi.org/10.1039/C7GC01925D]
[55]
Xu, J.; He, S.; Zhang, H.; Huang, J.; Lin, H.; Wang, X.; Long, J. J. Mater. Chem. A Mater. Energy Sustain., 2015, 3(48), 24261-24271.
[http://dx.doi.org/10.1039/C5TA06838J]
[56]
Jia, X.; Zhang, B.; Chen, C.; Fu, X.; Huang, Q. Carbohydr. Polym., 2021, 253117305
[http://dx.doi.org/10.1016/j.carbpol.2020.117305] [PMID: 33278956]
[57]
Guo, P.P.; He, Z.H.; Yang, S.Y.; Wang, W.; Wang, K.; Li, C.C.; Wei, Y.Y.; Liu, Z.T.; Han, B. Green Chem., 2022, 24(4), 1527-1533.
[http://dx.doi.org/10.1039/D1GC04284J]