Progress in Application of Organic Polymers Supported Rhodium Catalysts in Hydroformylation

  • Zong Lingbo ,
  • Chen Jianbin ,
  • Ren Xinyi ,
  • Zhang Guoying ,
  • Jia Xiaofei
Expand
  • a Shandong Key Laboratory of Biochemical Analysis, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao, Shandong 266042;
    b Shandong Provincial Key Laboratory of Molecular Engineering, School of Chemistry and Chemical Engineering, Qilu University of Technology, Jinan 250353;
    c Shanghai Key Laboratory of Green Chemistry and Chemical Process, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200241

Received date: 2020-03-03

  Revised date: 2020-05-01

  Online published: 2020-05-19

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21703116, 51702180) and the Open Fund of the Department of Chemistry, Qingdao University of Science and Technology (Nos. QUSTHX201932, QUSTHX202010).

Abstract

Hydroformylation is considered one of the most important homogenously catalyzed processes in dustry. Hydroformylation has been widely used in the production of aldehydes, and aldehydes can also be further converted into high value-added alcohols, acids and other derivatives. Compared with the homogeneous reaction, the heterogeneous catalysts present significant advantages in terms of recyclability, separation of catalysts and products and so on. In recent years, organic polymer-supported rhodium catalysts have shown excellent catalytic activity, high selectivity, and good recycleability in heterogeneous hydroformylation, and have attracted widespread attention. The research progress of the application of organic polymer supported catalysts in hydroformylation is summarized, including synthesis, material characteristics and application of supported catalysts. Finally, the prospect of the reaction is discussed.

Cite this article

Zong Lingbo , Chen Jianbin , Ren Xinyi , Zhang Guoying , Jia Xiaofei . Progress in Application of Organic Polymers Supported Rhodium Catalysts in Hydroformylation[J]. Chinese Journal of Organic Chemistry, 2020 , 40(8) : 2308 -2321 . DOI: 10.6023/cjoc202003006

References

[1] (a) van Leeuwen, P. W. N. M.; Claver, C. Rhodium catalyzed hydroformylation, Kluwer Academic Publishers, Dordrecht, 2000.
(b) Haumann, M.; Riisager, A. Chem. Rev. 2008, 108, 1474.
(c) Hebrard, F.; Kalck, P. Chem. Rev. 2009, 109, 4272.
(d) Franke, R.; Selent, D.; Borner, A. Chem. Rev. 2012, 112, 5675.
(e) Pospech, J.; Fleischer, I.; Franke, R.; Buchholz, S.; Beller, M. Angew. Chem., Int. Ed. 2013, 52, 2852.
[2] Roelen, O. U. S. 2327066, 1943[Chem. Abstr. 1944, 38, 363].
[3] Börner, A.; Franke, R. Hydroformylation:Funda Mentals, Processes, and Applications in Organic Synthesis, Wiley-VCH, Weinheim, 2016.
[4] (a) Casey, C. P.; Paulsen, E. L.; Beuttenmueller, E. W.; Proft, B. R.; Petrovich, L. M.; Matter, B. A.; Powell, D. R. J. Am. Chem. Soc. 1997, 119, 11817.
(b) Herrmann, W. A.; Kohlpaintner, C. W.; Herdtweck, E.; Kiprof, P. Inorg. Chem. 1991, 30, 4271.
(c) Yu, S.; Zhang, X.; Yan, Y.; Cai, C.; Dai, L.; Zhang, X. Chem. Eur. J. 2010, 16, 4938.
(d) Yan, Y.; Zhang, X.; Zhang, X. Adv. Synth. Catal. 2007, 349, 1582.
(e) Chen, C.; Li, P.; Hu, Z.; Wang, H.; Zhu, H.; Hu, X.; Wang, Y.; Lv, H.; Zhang, X. Org. Chem. Front. 2014, 1, 947.
[5] Klein, H.; Jackstell, R.; Wiese, K.-D.; Borgmann, C.; Beller, M. Angew. Chem., Int. Ed. 2001, 40, 3408.
[6] (a) Carbó, J. J.; Maseras, F.; Bo. C.; van Leeuwen, P. W. N. M. J. Am. Chem. Soc. 2001, 123, 7630.
(b) Kranenburg, M.; van der Burgt, Y. E. M.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Goubitz, K.; Fraanje, J. Organometallics 1995, 14, 3081.
(c) Van der Veen, L. A.; Boele, M. D. K.; Bregman, F. R.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Goubitz, K.; Fraanje, J.; Schenk, H.; Bo, C. J. Am. Chem. Soc. 1998, 120, 11616.
(d) van der Veen, L. A.; Kamer, P. C. J.; van Leeu wen, P. W. N. M. Angew. Chem., Int. Ed. 1999, 38, 336.
[7] Burke, P. M.; Garner, J. M.; Kreutzer, K. A.; Teunis sen, A. J. J. M.; Snijder, C. S.; Hansen, C. B. WO 97/33854, 1997.
[8] (a) Cunny, G. D.; Buchwald, S. L. J. Am. Chem. Soc. 1993, 115, 2066.
(b) Behr, A.; Obst, D.; Schulte, C. J. Mol. Catal. A-Chem. 2003, 206, 179.
[9] (a) van der Slot, S. C.; Duran, J.; Luten, J.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Organometallics 2002, 21 3873.
(b) Yan, Y.; Zhang, X.; Zhang, X. J. Am. Chem. Soc. 2006, 128, 16058.
(c) Yu, S.; Chie, Y.; Guan, Z.; Zou, Y.; Li, W.; Zhang, X. Org. Lett. 2009, 11, 241.
(d) Jia, X.; Wang, Z.; Xia, C.; Ding, K. Chem. Eur. J. 2012, 18, 15288.
(e) Ren, X.; Zheng, Z.; Zhang, L.; Wang, Z.; Xia, C.; Ding, K. Angew. Chem., Int. Ed. 2017, 56, 310.
(f) Jia, X.; Ren, X.; Wang, Z.; Xia, C.; Ding, K. Chin. J. Org. Chem. 2019, 39, 207(in Chinese) (贾肖飞, 任新意, 王正, 夏春谷, 丁奎岭, 有机化学, 2019, 39, 207.)
(g) Chen, C.; Qiao, Y.; Geng, H.; Zhang, X. Org. Lett. 2013, 15, 1048.
[10] (a) Li, C; Wang, W; Yan, L.; Ding, Y. Front. Chem. Sci. Eng. 2018, 12, 113.
(b) Zhang, J.; Sun, P.; Zhao, Z. L.; Li, F. W. Chin. Sci. Bull. 2019, 64, 3173.
[11] (a) Arhancet, J. P.; Davis, M. E.; Merola, J. S.; Hanson, B. E. Nature 1989, 339, 454.
(b) Chaudhari, R. V.; Bhanage, B. M.; Deshpande, R. M. Nature 1995, 373, 501.
(c) Sharma, S. K.; Jasra, R. V. Catal. Today 2015, 247, 70.
(d) Hapiot, F.; Ponchel, A.; Tilloy, S.; Monflier, Compt. Rend. Chim. 2011, 14, 149.
(e) Paganelli, S.; Piccolo, O.; Pontini, P.; Tassini, R.; Rathod, V. D. Catal. Today 2015, 247, 64.
[12] (a) Horváth, I. T.; Kiss, G.; Cook, R. A., Bond, J. E.; Stevens, P. A.; Rábai, J.; Mozeleski, E. J. J. Am. Chem. Soc. 1998, 120, 3133.
(b) Cornils, B. Angew. Chem., Int. Ed. 1997, 36, 2057.
(c) Chen, W. P.; Xu, L. J.; Xiao, J. L. Chem. Commun. 2000, 10, 839.
(d) Horvath, I. T.; Rabai, J. Science 1994, 266, 72.
[13] (a) Mehnert, C. P.; Cook, R. A.; Dispenziere, N. C.; Afeworki, M. J. Am. Chem. Soc. 2002, 124, 12932.
(b) Riisager, A.; Fehrmann, R.; Flicker, S.; van Hal, R.; Haumann, M.; Wasserscheid, P. Angew. Chem., Int. Ed. 2005, 44, 815.
(c) Jin, X.; Feng, J.; Ma, Q.; Song, H.; Liu, Q.; Xu, B.; Zhang, M.; Li, S.; Yu, S. Green Chem. 2019, 21, 3267.
(d) Walter, S.; Spohr, H.; Franke, R.; Hieringer, W.; Wasserscheid, P.; Haumann, M. ACS Catal. 2017, 7, 1035.
[14] (a) David, J.; Cole-Hamilton, O. J. Science 2003, 299, 1702.
(b) Jessop, P. G.; Hsion, Y.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 344.
(c) Kainz, S., Koch, D.; Baumann, W.; Leitner, W. Angew. Chem., Int. Ed. 1997, 36, 1628.
(d) Koeken, A. C. J.; Smeets, N. M. B. Catal. Sci. Technol. 2013, 3, 1036.
(e) Estorach, C. T.; Orejon, A.; Masdeu-Bulto, A. M. Green Chem. 2008, 10, 545.
[15] Gärtner, L.; Cornils, B.; Lappe, P. (to Ruhrchemie AG) EP 0107006, 1983[Chem. Abstr. 1984, 101, 55331].
[16] (a) Kuntz, E. G. CHEMTECH 1987, 17, 570.
(b) Cornils, B.; Kuntz, E. G. J. Organomet. Chem.1995, 502, 177.
[17] Herrmann, W. A.; Kohlpaintner, C. W.; Bahrmann, H.; Konkol, W. J. Mol. Catal. 1992, 73, 191.
[18] Bahmann, H.; Bergrath, K.; Kleiner, H.-J.; Lappe, P.; Naumann, C.; Peters, D.; Regnat, D. J. Organomet. Chem. 1996, 520, 97.
[19] (a) Vunain, E.; Ncube, P.; Jalama, K.; Meijboom, R. J. Porous Mater. 2018, 25, 303.
(b) Malihan, L. B.; Nisola, G. M.; Mittal, N.; Lee, S.-P.; Seo, J. G.; Kim, H.; Chung, W. J. RSC Adv. 2016, 6, 33901.
(c) Sudheesh, N.; Parmar, J. N.; Shukla, R. S. Appl. Catal. A Gen. 2012, 415, 124.
(d) Yan, L.; Ding, Y. J.; Lin, L. W.; Zhu, H. J.; Yin, H. M.; Li, X. M.; Lu, Y. J. Mol. Catal. A-Chem. 2009, 300, 116.
[20] (a) Wolf, P.; Logemann, M.; Schorner, M.; Keller, L.; Haumann, M.; Wessling, M. RSC Adv. 2019, 9, 27732.
(b) Weiss, A.; Munoz, M.; Haas, A.; Rietzler, F.; Steinruck, H.-P.; Haumann, M.; Wasserscheid, P.; Etzold, B. J. ACS Catal. 2016, 6, 2280.
(c) Weiß, A.; Giese, M.; Lijewski, M.; Franke, R.; Wasserscheid, P.; Haumann, M. Catal. Sci. Technol. 2017, 7, 5562.
[21] (a) Chuai, H. Y.; Su, P.; Liu, H.; Zhu, B.; Zhang, S.; Huang, W. Catalysts 2019, 9, 194.
(b) Liu, J.; Yan, L.; Ding, Y.; Jiang, M.; Dong, W.; Song, X.; Liu, T.; Zhu, H. Appl. Catal. A Gen. 2015, 492, 127.
[22] (a) Nozaki, K.; Itoi, Y.; Shibahara, F.; Shirakawa, E.; Ohta, T.; Takaya, H.; Hiyama, T. J. Am. Chem. Soc. 1998, 120, 4051.
(b) Nozaki, K.; Shibahara, F.; Itoi, Y.; Shirakawa, E.; Ohta, T.; Takaya, H.; Hiyama, T. Bull. Chem. Soc. Jpn. 1999, 72, 1911.
[23] (a) Shibahara, F.; Nozaki, K.; Hiyama, T. J. Am. Chem. Soc. 2003, 125, 8555.
(b) Nozaki, K.; Shibahara, F.; Hiyama, T. Chem. Lett. 2000, 694.
[24] (a) Stiriba, S. E.; Slagt, M. Q.; Kautz, H.; Klein Gebbink, R. J. M.; Thomann, R.; Frey, H.; van Koten, G. Chem. Eur. J. 2004, 10, 1267.
(b) Kumar, K. R.; Kizhakkedathu, J. N.; Brooks, D. E. Macromol. Chem. Phys. 2004, 205, 567.
(c) Wilms, D.; Stiriba, S. E.; Frey, H. Acc. Chem. Res. 2010, 43, 129.
(d) Slagt, M. Q.; Stiriba, S.-E.; Kautz, H.; Klein Gebbink, R. J. M.; Frey, H.; van Koten, G. Organometallics 2004, 23, 1525.
[25] Ricken, S.; Osinski, P. W.; Eilbracht, P.; Haag, R. J. Mol. Catal. A-Chem. 2006, 257, 78.
[26] (a) Wang, H.; Sun, W.; Xia, C. J. Mol. Catal. A:Chem. 2003, 206, 199.
(b) Makhubela, B. C. E.; Jardine, A.; Smith, G. S. Appl. Catal. A Gen. 2011, 393, 231.
(c) Hertrich, M. F.; Scharnagl, F. K.; Pews-Davtyan, A.; Kreyenschulte, C. R.; Lund, H.; Bartling, S.; Jackstell, R.; Beller, M. Chem.-Eur. J. 2019, 25, 5534.
(d) Molnar, A. Coord. Chem. Rev. 2019, 388, 126.
(e) Antony, R.; Arun, T.; Manickam, S. T. D. Int. J. Biol. Macromol. 2019, 129, 615.
[27] Makhubela, B. C. E.; Jardine, A.; Smith, G. S. Green Chem. 2012, 14, 338.
[28] (a) Shifrina, Z. B.; Matveeva, V. G.; Bronstein, L. M. Chem. Rev. 2020, 120, 1350.
(b) Kramer, S.; Bennedsen, N. R.; Kegnæs, S. ACS Catal. 2018, 8, 6961.
(c) Sun, Q.; Dai, Z.; Meng, X.; Xiao, F.-S. Chem. Soc. Rev. 2015, 44, 6018.
(d) Kaur, P.; Hupp, J. T.; Nguyen, S. B. T. ACS Catal. 2011, 1, 819.
[29] Sun, Q.; Jiang, M.; Shen, Z.; Jin, Y.; Pan, S.; Wang, L.; Meng, X.; Chen, W.; Ding, Y.; Li, J.; Xiao, F.-S. Chem. Commun. 2014, 50, 11844.
[30] Jiang, M.; Yan, L.; Ding, Y.; Sun, Q.; Liu, J.; Zhu, H.; Lin, R.; Xiao, F.; Jiang, Z.; Liu, J. J. Mol. Catal. A:Chem. 2015, 404, 211.
[31] Sun, Q.; Aguila, B.; Verma, G.; Liu, X.; Dai, Z.; Deng, F.; Meng, X.; Xiao, F.-S.; Ma, S. Chem 2016, 1, 628.
[32] Tang, Y.; Dong, K.; Wang, S.; Sun, Q.; Meng, X.; Xiao, F.-S. Mol. Catal. 2019, 474, 110408.
[33] Sun, Q.; Dai, Z.; Liu, X.; Sheng, N.; Deng, F.; Meng, X.; Xiao, F. S. J. Am. Chem. Soc. 2015, 137, 5204.
[34] Li, C.; Sun, K.; Wang, W.; Yan, L.; Sun, X.; Wang, Y.; Xiong, K.; Zhan, Z.; Jiang, Z.; Ding, Y. J. Catal. 2017, 353, 123.
[35] Li, C.; Xiong, K.; Yan, L.; Jiang, M.; Song, X.; Wang, T.; Chen, X.; Zhan, Z.; Ding, Y. Catal. Sci. Technol. 2016, 6, 2143.
[36] Wang, Y.; Yan, L.; Li, C.; Jiang, M.; Wang, W.; Ding, Y. Appl. Catal. A Gen. 2018, 551, 98.
[37] Wang, Y.; Yan, L.; Li, C.; Jiang, M.; Zhao, Z.; Hou, G.; Ding, Y. J. Catal. 2018, 368, 197.
[38] Jia, X.; Liang, Z.; Chen, J.; Lv, J.; Zhang, K.; Gao, M.; Zong, L.; Xie, C. Org. Lett. 2019, 21, 2147.
[39] (a) Johnson, J. R.; Cuny, G. D.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1760.
(b) Agabekov, V.; Seiche, W.; Breit, B. Chem. Sci. 2013, 4, 2418.
(c) Fang, X.; Zhang, M.; Jackstell, R.; Beller, M. Angew. Chem., Int. Ed. 2013, 52, 4645.
(d) Zhang, Z.; Wang, Q.; Chen, C.; Han, Z.; Dong, X.; Zhang, X. Org. Lett. 2016, 18, 3290.
[40] Liang, Z.; Chen, J.; Chen, X.; Zhang, K.; Lv, J.; Zhao, H.; Zhang, G.; Xie, C.; Zong, L.; Jia, X. Chem. Commun. 2019, 55, 13721.
[41] Dong, K.; Sun, Q.; Tang, Y.; Shan, C.; Aguila, B.; Wang, S.; Meng, X.; Ma, S.; Xiao, F.-S. Nat. Commun. 2019, 10, 3059.
[42] Wang, T.; Wang, W.; Lyu, Y.; Xiong, K.; Li, C.; Zhang, H.; Zhan, Z.; Jiang, Z.; Ding, Y. Chin. J. Catal. 2017, 38, 691.
Outlines

/