Abstract
1,3,5-Triazine functionalized nanoporous polymer (PDVB-triazine-xs, where x stands for the molar ratio of DVB and triazine) was synthesized from copolymerization of 1,3,5-triacryloylhexahydro1,3,5-triazine with divinylbenzene (DVB) cross-linker under solvothermal conditions. The resultant PDVB-triazine-xs act as efficient supports for Pd(OAc)2, which gives the Pd/PDVB-triazine-xs catalyst. Characterizations by N2 isotherms, TEM images, and solid NMR 13C spectrum show that Pd/PDVB-triazine-xs has large surface areas, abundant nanopores, and successful copolymerization of DVB with triazine functional monomer, which showed a high cross linking degree. XRD and elemental maps show Pd was successfully loaded into PDVB-triazine-xs supports, which showed very good dispersion in the samples. Pd/PDVB-triazine-xs showed excellent catalytic activity and good recyclability in Suzuki–Miyaura cross coupling reaction. The preparation of Pd/PDVB-triazine-xs will develop functional nanoporous polymer based catalysts or catalyst supports in the Suzuki–Miyaura reaction.
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Corma, A., Chem. Rev., 1997, vol. 97, p. 2373.
Shi, J.L., Chem. Rev., 2013, vol. 113, p. 2139.
Zhao, D.Y., Huo, Q.S., Feng, J.L., Chmelka, B.F., and Stucky, G.D., J. Am. Chem. Soc., 1998, vol. 120, p. 6024.
Yang, Q., Wang, S.C., Fan, P.W., Wang, L.F., Di, Y., Lin, K.F., and Xiao, F.S., Chem. Mater., 2005, vol. 17, p. 5999.
Liu, F.J., Li, C.J., Ren, L.M., Meng, X.J., Zhang, H., and Xiao, F.S., J. Mater. Chem., 2009, vol. 19, p. 7921.
Liu, F.J., Wang, L., Sun, Q., Zhu, L.F., Meng, X.J., and Xiao, F.S., J. Am. Chem. Soc., 2012, vol. 134, p. 16948.
Liu, F.J., Willhammar, T., Wang, L., Zhu, L.F., Sun, Q., Meng, X.J., Carrillo-Cabrera, W., Zou, X.D., and Xiao, F.S., J. Am. Chem. Soc., 2012, vol. 134, p. 4557.
Liu, F.J., Kamat, R., Noshadi, I., Peck, D., Parnas, R., Zheng, A.M., Qi, C.Z., and Lin, Y., Chem. Commun., 2013, vol. 49, p. 8456.
Liu, F.J., Zheng, A.M., Noshadi, I., and Xiao, F.S., App. Catal., B, 2013, vol. 136–137, pp. 193–201.
Yang, P.D., Zhao, D.Y., Margolese, D.I., Chmelka, B.F., and Stucky, G.D., Nature, 1998, vol. 396, p. 152.
Ryoo, R., Joo, Sh., and Jun, S., J. Phys. Chem. B, 1999, vol. 103, p. 7743.
Johnson, S.A., Ollivier, P.J., and Mallouk, T.E., Science, 1999, vol. 283, p. 963.
Meng, Y., Gu, D., Zhang, F.Q., Shi, Y.F., Yang, H.F., Li, Z., Yu, C.Z., Tu, B., and Zhao, D.Y., Angew. Chem., Int. Ed. Engl., 2005, vol. 44, p. 7053.
Liu, F.J., Kong, W.P., Qi, C.Z., Zhu, L.F., and Xiao, F.S., ACS Catal., 2012, vol. 2, p. 565.
Liu, F.J., Li, W., Sun, Q., Zhu, L.F., Meng, X.J., Guo, Y.H., and Xiao, F.S., ChemSusChem, 2011, vol. 4, p. 1059.
Kim, J.Y., Yoon, S.B., Kooli, F., and Yu, J.S., J. Mater. Chem., 2001, vol. 11, p. 2912.
Wu, D.C., Xu, F., Sun, B., Fu, R.W., He, H.K., and Matyjaszewski, K., Chem. Rev., 2012, vol. 112, p. 3959.
Xing, R., Liu, N., Liu, Y.M., Wu, H.H., Jiang, Y.W., Chen, L., He, M.Y., and Wu, P., Adv. Funct. Mater., 2007, vol. 17, p. 2455.
Xing, R., Liu, Y.M., Wu, H.H., Li, X.H., He, M.Y., and Wu, P., Chem. Commun., 2008, vol. 44, p. 6297.
Wan, Y., Wang, H.Y., Zhao, Q.F., Klingstedt, M., Terasaki, O., and Zhao, D.Y., J. Am. Chem. Soc., 2009, vol. 131, p. 4541.
Miyaura, N. and Suzuki, A., Chem. Rev., 1995, vol. 95, p. 2457.
Metal-Catalyzed Cross-Coupling Reactions, de Meijere, A. and Diederich, F., Eds., Weinheim: Wiley–VCH, 2004.
Wu, X.F., Anbarasan, P., Neumann, H., and Beller, M., Angew. Chem., Int. Ed. Engl., 2010, vol. 49, p. 9047.
Liu, F.J., Feng, G.F., Lin, M.Y., Wang, C., Hu, B.W., and Qi, C.Z., J. Colloid Interface Sci., 2014, vol. 435, p. 83.
Mu, B., Li, J., Han, Z., and Wu, Y., J. Organomet. Chem., 2012, vol. 700, p. 117.
Das, P., Sarmah, C., Tairai, A., and Bora, U., Appl. Organomet. Chem., 2011, vol. 25, p. 283.
Amoroso, F., Colussi, S., Del Zotto, A., Llorca, J., and Trovarelli, A., Catal. Commun., 2011, vol. 12, p. 563.
He, Y. and Cai, C., Catal. Lett., 2010, vol. 140, p. 153.
Durap, F., Rakap, M., Aydemir, M., and Ozkar, S., Appl. Catal., A, 2010, vol. 382, p. 339.
Maegawa, T., Kitamura, Y., Sako, S., Udzu, T., Sakurai, A., Tanaka, A., Kobayashi, Y., Endo, K., Bora, U., Kurita, T., Kozaki, A., Monguchi, Y., and Sajiki, H., Chem. Eur. J., 2007, vol. 13, p. 5937.
Deng, C.-L., Guo, S.-M., Xie, Y.-X., and Li, J.-H., Eur. J. Org. Chem, 2007, p. 1457.
Jin, M.J., Taher, A., Kang, H.J., Choi, M., and Ryoo, R., Green Chem., 2009, vol. 11, p. 309.
Yang, Q., Ma, S.M., Li, J.X., Xiao, F.S., and Xiong, H., Chem. Commun., 2006, vol. 42, p. 2495.
Oh, J., Lee, S., Zhang, K., Hwang, J.O., Han, J., Park, G., Kim, S.O., Park, J.H., and Park, S., Carbon, 2014, vol. 66, p. 119.
Liu, F.J., Meng, X.J., Zhang, Y.L., Ren, L.M., Nawaz, F., and Xiao, F.-S., J. Catal., 2010, vol. 271, p. 52.
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Feng, G., He, J., Deng, W. et al. Pd(AcO)2 supported by 1,3,5-triazine functionalized nanoporous polymers: Efficient and recyclable heterogeneous catalysts for Suzuki–Miyaura reaction. Kinet Catal 56, 703–711 (2015). https://doi.org/10.1134/S0023158415060026
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DOI: https://doi.org/10.1134/S0023158415060026