A Pd-metalated porous organic polymer as a highly efficient heterogeneous catalyst for C-C couplings

doi:10.1016/S1872-2067(15)60952-4

Chinese Journal of Catalysis ›› 2016, Vol. 37 ›› Issue (1): 54-60.DOI: 10.1016/S1872-2067(15)60952-4

• Special Column on New Porous Catalytic Materials • Previous Articles Next Articles

A Pd-metalated porous organic polymer as a highly efficient heterogeneous catalyst for C-C couplings

Zhifeng Dai, Fang Chen, Qi Sun, Yanyan Ji, Liang Wang, Xiangju Meng, Feng-Shou Xiao

Key Laboratory of Applied Chemistry of Zhejiang Province and Department of Chemistry, Zhejiang University, Hangzhou 310028, Zhejiang, China

Received:2015-05-20 Revised:2015-06-28 Online:2015-12-26 Published:2015-12-26
Supported by:
This work was supported by the National Natural Foundation of China (21422306, 21203165, 21403193) and the Fundamental Research Funds for the Central Universities (2015XZZX004-04).

Abstract

Abstract:

An efficient catalyst system based on a Pd-metalated porous organic polymer bearing phenanthroline ligands was designed and synthesized. This catalyst was applied to various C-C bond-forming reactions, including the Suzuki, Heck and Sonogashira couplings, and afforded the corresponding products while exhibiting excellent activities and selectivities. More importantly, this catalyst can be readily recycled. These features show that such catalysts have significant potential applications in the future.

Key words: Porous organic polymer, Phenanthroline ligand, Carbon-carbon couplings, Pd-based heterogeneous catalyst

Zhifeng Dai, Fang Chen, Qi Sun, Yanyan Ji, Liang Wang, Xiangju Meng, Feng-Shou Xiao. A Pd-metalated porous organic polymer as a highly efficient heterogeneous catalyst for C-C couplings[J]. Chinese Journal of Catalysis, 2016, 37(1): 54-60.

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References

[1] F. Diederich, A. de Meijere, Metal-Catalyzed Cross-Coupling Reactions, 2nd ed., Wiley-VCH, Weinheim, 2004, 4.
[2] L. X. Yin, J. Liebscher, Chem. Rev., 2007, 107, 133.
[3] N. Miyaura, A. Suzuki, Chem. Rev., 1995, 95, 2457.
[4] C. M. Wei, C. J. Li, J. Am. Chem. Soc., 2003, 125, 9584.
[5] J. Magano, J. R. Dunetz, Chem. Rev., 2011, 111, 2177.
[6] N. E. Leadbeater, M. Marco, Chem. Rev., 2002, 102, 3217.
[7] W. Watanabe, T. Maekawa, Y. Miyazaki, T. Kida, K. Takeshita, A. Mori, Chem Asian J., 2012, 7, 1679.
[8] M. Bakherad, A. Keivanloo, S. Samangooei, Chin. J. Catal., 2014, 35, 324.
[9] C. E. Garrett, K. Prasad, Adv. Synth. Catal., 2004, 346, 889.
[10] C. J. Welch, J. Albaneze-Walker, W. R. Leonard, M. Biba, J. DaSilva, D. Henderson, B. Laing, D. J. Mathre, S. Spencer, X. D. Bu, T. B. Wang, Org. Process Res. Dev., 2005, 9, 198.
[11] H. U. Blaser, A. Indolese, A. Schnyder, H. Steiner, M. Studer, J. Mol. Catal. A, 2001, 173, 3.
[12] B. M. Bhanage, M. Arai, Catal. Rev., 2001, 43, 315.
[13] X. Jin, V. V. Balasubramanian, S. T. Selvan, D. P. Sawant, M. A. Chari, G. Q. Lu, A. Vinu, Angew. Chem. Int. Ed., 2009, 48, 7884.
[14] M. Kawaguchi, S. Yagi, H. Enomoto, Carbon, 2004, 42, 345.
[15] Q. H. Fan, Y. M. Li, A. S. C. Chan, Chem. Rev., 2002, 102, 3385.
[16] S. Minakata, M. Komatsu, Chem. Rev., 2009, 109, 711.
[17] D. E. De Vos, M. Dams, B. F. Sels, P. A. Jacobs, Chem. Rev., 2002, 102, 3615.
[18] A. Taguchi, F. Schuth, Microporous Mesoporous Mater., 2005, 77, 1.
[19] M. Hartmann, Chem. Mater., 2005, 17, 4577.
[20] A. Corma, H. Garcia, Adv. Synth. Catal., 2006, 348, 1391.
[21] A. Thomas, Angew. Chem. Int. Ed., 2010, 49, 8328.
[22] Q. Sun, M. Jiang, Z. J. Shen, Y. Y. Jin, S. X. Pan, L. Wang, X. J. Meng, W. Z. Chen, Y. J. Ding, J. X. Li, F-S. Xiao, Chem. Commun., 2014, 50, 11844.
[23] Q. Sun, Z. F. Dai, X. L. Liu, N. Sheng, F. Deng, X. J. Meng, F-S. Xiao, J. Am. Chem. Soc., 2015, 137, 5204.
[24] Q. Sun, X. J. Meng, X. L. Liu, X. M. Zhang, Y. Yang, Q. H. Yang, F-S. Xiao, Chem. Commun., 2012, 48, 10505.
[25] Y. Huangfu, Q. Sun, S. X. Pan, X. J. Meng, F-S. Xiao, ACS Catal., 2015, 5, 1556.
[26] C. Bleschke, J. Schmidt, D. S. Kundu, S. Blechert, A. Thomas, Adv. Synth. Catal., 2011, 353, 3101.
[27] J. D. Crowley, S. M. Goldup, N. D. Gowans, D. A. Leigh, V. E. Ronaldson, A. M. Z. Slawin, J. Am. Chem. Soc., 2010, 132, 6243.
[28] T. Hamada, X. Ye, S. S. Stahl, J. Am. Chem. Soc., 2008, 130, 833.
[29] M. Boltz, A. Blanc, G. Laugel, P. Pale, B. Louis, Chin. J. Catal., 2011, 32, 807.
[30] J. L. Hu, Y. L. Gu, Z. H. Guan, J. J. Li, W. L. Mo, T. Li, G. X. Li, ChemSusChem, 2011, 4, 1767.
[31] Y. X. Gao, G. Wang, L. Chen, P. X. Xu, Y. F. Zhao, Y. B. Zhou, L. B. Han, J. Am. Chem. Soc., 2009, 131, 7956.
[32] Q. Sun, Z. F. Lv, Y. Y. Du, Q. M. Wu, L. Wang, L. F. Zhu, X. J. Meng, W. Z. Chen, F-S. Xiao, Chem. Asian J., 2013, 8, 2822.
[33] J. P. Lecomte, A. Kirsch-De Mesmaeker, M. Demeunynck, J. Lhomme, J. Chem. Soc., Faraday Trans., 1993, 89, 3261.
[34] W. H. Lin, W. L. Sun, J. Yang, Q. H. Sun, Z. Q. Shen, J. Phys. Chem. C, 2009, 113, 16884.
[35] M. B. Majewski, N. R. de Tacconi, F. M. MacDonnell, M. O. Wolf, Inorg. Chem., 2011, 50, 9939.
[36] X. Y. Liu, Y. L. Hu, B. Y. Wang, Z. X. Su, Synth. Metals, 2009, 159, 1557.
[37] P. Siemsen, R. C. Livingston, F. Diederich, Angew. Chem. Int. Ed., 2000, 39, 2632
[38] A. Elangovan, Y. H. Wang, T. I. Ho, Org. Lett., 2003, 5, 1841.
[39] S. Thorand, N. Krause, J. Org. Chem., 1998, 63, 8551.
[40] F. J. Liu, L. Wang, Q. Sun, L. F. Zhu, X. J. Meng, F. S. Xiao, J. Am. Chem. Soc., 2012, 134, 16948.

A Pd-metalated porous organic polymer as a highly efficient heterogeneous catalyst for C-C couplings

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