Progress in Application of Organic Polymers Supported Rhodium Catalysts in Hydroformylation
- Corresponding author: Jia Xiaofei, jiaxiaofei139@163.com
Citation:
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
(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.
Roelen, O. U. S. 2327066, 1943[Chem. Abstr. 1944, 38, 363].
Börner, A.; Franke, R. Hydroformylation: Funda Mentals, Processes, and Applications in Organic Synthesis, Wiley-VCH, Weinheim, 2016.
(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.
Klein, H.; Jackstell, R.; Wiese, K.-D.; Borgmann, C.; Beller, M. Angew. Chem., Int. Ed. 2001, 40, 3408.
(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.
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.
(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.
(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.
(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.
(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.
(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.
(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
(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.
Gärtner, L.; Cornils, B.; Lappe, P. (to Ruhrchemie AG) EP 0107006, 1983[Chem. Abstr. 1984, 101, 55331].
(a) Kuntz, E. G. CHEMTECH 1987, 17, 570.
(b) Cornils, B.; Kuntz, E. G. J. Organomet. Chem.1995, 502, 177.
Herrmann, W. A.; Kohlpaintner, C. W.; Bahrmann, H.; Konkol, W. J. Mol. Catal. 1992, 73, 191.
Bahmann, H.; Bergrath, K.; Kleiner, H.-J.; Lappe, P.; Naumann, C.; Peters, D.; Regnat, D. J. Organomet. Chem. 1996, 520, 97.
(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.
(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) Weiβ A.; Giese, M.; Lijewski, M.; Franke, R.; Wasserscheid, P.; Haumann, M. Catal. Sci. Technol. 2017, 7, 5562.
(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.
(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.
(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.
(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.
Ricken, S.; Osinski, P. W.; Eilbracht, P.; Haag, R. J. Mol. Catal. A-Chem. 2006, 257, 78.
(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.
Makhubela, B. C. E.; Jardine, A.; Smith, G. S. Green Chem. 2012, 14, 338.
(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.
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.
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.
Sun, Q.; Aguila, B.; Verma, G.; Liu, X.; Dai, Z.; Deng, F.; Meng, X.; Xiao, F.-S.; Ma, S. Chem 2016, 1, 628.
Tang, Y.; Dong, K.; Wang, S.; Sun, Q.; Meng, X.; Xiao, F.-S. Mol. Catal. 2019, 474, 110408.
Sun, Q.; Dai, Z.; Liu, X.; Sheng, N.; Deng, F.; Meng, X.; Xiao, F. S. J. Am. Chem. Soc. 2015, 137, 5204.
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.
Li, C.; Xiong, K.; Yan, L.; Jiang, M.; Song, X.; Wang, T.; Chen, X.; Zhan, Z.; Ding, Y. Catal. Sci. Technol. 2016, 6, 2143.
Wang, Y.; Yan, L.; Li, C.; Jiang, M.; Wang, W.; Ding, Y. Appl. Catal. A Gen. 2018, 551, 98.
Wang, Y.; Yan, L.; Li, C.; Jiang, M.; Zhao, Z.; Hou, G.; Ding, Y. J. Catal. 2018, 368, 197.
Jia, X.; Liang, Z.; Chen, J.; Lv, J.; Zhang, K.; Gao, M.; Zong, L.; Xie, C. Org. Lett. 2019, 21, 2147.
(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.
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.
Dong, K.; Sun, Q.; Tang, Y.; Shan, C.; Aguila, B.; Wang, S.; Meng, X.; Ma, S.; Xiao, F.-S. Nat. Commun. 2019, 10, 3059.
Wang, T.; Wang, W.; Lyu, Y.; Xiong, K.; Li, C.; Zhang, H.; Zhan, Z.; Jiang, Z.; Ding, Y. Chin. J. Catal. 2017, 38, 691.
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