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Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 07: 1369 - 1381

DOI: https://doi.org/10.6023/cjoc201304005

Reviews

Recent Advances in Rh-Catalyzed Asymmetric Hydroformylation of Olefins

  • Jia Xiaofei ,
  • Wang Zheng ,
  • Xia Chungu ,
  • Ding Kuiling
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  • a State Key Laboratory of Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000;
    b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received date: 2013-04-06

  Revised date: 2013-04-22

  Online published: 2013-04-24

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21172237, 21121062, 21032009).

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Abstract

Hydroformylation is one of the most important processes of homogeneous catalysis in industry. Asymmetric hydroformylation (AHF) of prochiral alkenes provides an efficient way to the synthesis of optically active aldehydes, which are versatile chiral intermediates for pharmaceuticals, agrochemicals, and other fine chemicals. So far, most of methods reported were focused on the use of Rh(I)-based catalysts, by virtue of their high catalytic activity and excellent chemoselectivity for the aldehydes. A key issue in searching for efficient asymmetric hydroformylation catalysts is the development of new chiral ligands. A number of chiral phosphorus ligands have been successfully developed for Rh(I)-catalyzed AHF reactions. In this review, the recent advances in the development of chiral ligands for the Rh-catalyzed asymmetric hydroformylaion of olefins have been surveyed.

Key words： aldehyde; asymmetric catalysis; chiral phosphine ligand; hydroformylation; olefin, rhodium

Cite this article

Jia Xiaofei , Wang Zheng , Xia Chungu , Ding Kuiling . Recent Advances in Rh-Catalyzed Asymmetric Hydroformylation of Olefins[J]. Chinese Journal of Organic Chemistry, 2013 , 33(07) : 1369 -1381 . DOI: 10.6023/cjoc201304005

References

[1] (a) Claver, C.; van Leeuwen, P. W. N. M. Rhodium Catalyzed Hydroformylation, Kluwer Academic Publishers, Dordrecht, 2002. (b) Franke, R.; Selent, D.; Börner, A. Chem. Rev. 2012, 112, 5675. (c) Su, K.; Jiang, H.; Zhu, D.; Fu, H.; Zheng, X.; Yuan, M.; Li, R.; Chen, H. Acta Chim. Sinica, 2013, 71, 844.
[2] Naqvi, S. Oxo Alcohols. Process Economics Program Report 21E, SRI Consulting, Menlo Park, CA, 2010.
[3] (a) Agbossou, F.; Carpentier, J. F.; Mortreaux, A. Chem. Rev. 1995, 95, 2485. (b) Gual, A.; Godard, C.; Castillón, S.; Claver, C. Tetrahedron: Asymmetry 2010, 21, 1135.
[4] Botteghi, C.; Paganelli, S.; Schionato, A.; Marchetti, M. Chirality 1991, 3, 355.
[5] Botteghi, C.; Consiglio, G.; Pino, P. Chimia 1972, 26, 141.
[6] (a) Ogata, I.; Ikeda, Y. Chem. Lett. 1972, 487. (b) Tanaka, M.; Watanabe, Y.; Mitsudo, T.-A,; Yamamoto, K.; Takeeami, Y. Chem. Lett. 1972, 483.
[7] Salomon, C.; Consiglio, G.; Botteghi, C.; Pino, P. Chimia 1973, 27, 215.
[8] Stille, J. K.; Su, H.; Brechot, P.; Parrinello, G.; Hegedus, L. S. Organometallics 1991, 10, 1183.
[9] (a) Sakai, N.; Mano, S.; Nozaki, K.; Takaya, H. J. Am. Chem. Soc. 1993, 115, 7033. (b) Nozaki, K.; Nanno, T.; Takaya, H. J. Organomet. Chem. 1997, 527, 103. (c) Lambers-Verstappen, M. M. H.; de Vries, J. G. Adv. Synth. Catal. 2003, 345, 478.
[10] (a) Saskai, N.; Nozaki, K.; Takaya, H. J. Chem. Soc., Chem. Commun. 1994, 395. (b) Nozaki, K.; Sakai, N.; Nanno, T.; Higashijima, T.; Mano, S.; Horiuchi, T.; Takaya, H. J. Am. Chem. Soc. 1997, 119, 4413. (c) Nozaki, K.; Takaya, H.; Hiyama, T. Top. Catal. 1997, 4, 175.
[11] Hoiuchi, T.; Ota, T.; Shirakawa, E.; Nozaki, K.; Takaya, H. J. Org. Chem. 1997, 62, 4285.
[12] Mazuela, J.; Coll, M.; Pàmies, O.; Diéguez, M. J. Org. Chem. 2009, 74, 5440.
[13] Tanaka, R.; Nakano, K.; Nozaki, K. J. Org. Chem. 2007, 72, 8671.
[14] Liu, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 10772.
[15] (a) Yan, Y.; Zhang, X. J. Am. Chem. Soc. 2006, 128, 7198. (b) Zhang, X.; Cao, B.; Yan, Y.; Yu, S.; Ji, B.; Zhang, X. Chem. Eur. J. 2010, 16, 871.
[16] Zhang, X.; Cao, B.; Yu, S.; Zhang, X. Angew. Chem., Int. Ed. 2010, 49, 4047.
[17] Chikkali, S. H.; Bellini, R.; de Bruin, B.; van der Vlugt, J. I.; Reek, J. N. H. J. Am. Chem. Soc. 2012, 134, 6607.
[18] Noonan, G. M.; Fuentes, J. A.; Cobley, C. J.; Clarke, M. L. Angew. Chem., Int. Ed. 2012, 51, 2477.
[19] (a) Babin, J. E.; Whiteker, G. T. US 5360938, 1993 [Chem. Abstr. 1995, 122, 186609]. (b) Buisman, G. J. H.; Vos, E. J.; Kamer, P. C. J.; Van Leeuwen, P. W. N. M. J. Chem. Soc., Dalton Trans. 1995, 409.
[20] Clark, T. P.; Landis, C. R.; Freed, S. L.; Klosin, J.; Abboud, K. A. J. Am. Chem. Soc. 2005, 127, 5040.
[21] Diéguez, M.; Pàmies, O.; Ruiz, A.; Castillón, S.; Claver, C. Chem. Eur. J. 2001, 7, 3086.
[22] (a) Diéguez, M.; Pàmies, O.; Claver, C. Chem. Commun. 2005, 1221. (b) Gual, A.; Godard, C.; Castillón, S.; Claver, C. Adv. Synth. Catal. 2010, 352, 463.
[23] (a) Cobley, C. J.; Klosin, J.; Qin, C.; Whiteker, G. T. Org. Lett. 2004, 6, 3277. (b) Cobley, C. J.; Gardner, K.; Klosin, J.; Praquin, C.; Hill, C.; Whiteker, G. T.; Zanotti-Gerosa, A. J. Org. Chem. 2004, 69, 4031.
[24] Zhao, B.; Peng, X.; Wang, W.; Xia, C.; Ding, K. Chem. Eur. J. 2008, 14, 7847.
[25] Peng, X.; Wang, Z.; Xia, C.; Ding, K. Tetrahedron Lett. 2008, 49, 4862.
[26] Breeden, S.; Cole-Hamilton, D. J.; Foster, D. F.; Schwarz, G. J.; Wills, M. Angew. Chem., Int. Ed. 2000, 39, 4106.
[27] (a) Jiang, Y.; Xue, S.; Li, Z.; Deng, J.; Mi, A.; Chan, A. S. C. Tetrahedron: Asymmetry 1998, 9, 3185. (b) Jiang, Y.; Xue, S.; Yu, K.; Li, Z.; Deng, J.; Mi, A.; Chan, A. S. C. J. Organomet. Chem. 1999, 586, 159. (c) Yan, M.; Li, X.-S.; Chan, A. S. C. Chin. J. Chem. 2004, 22, 203.
[28] (a) Klosin, J.; Landis, C. R. Acc. Chem. Res. 2007, 40, 1251. (b) Thomas, P. J.; Axtell, A. T.; Klosin, J.; Peng, W.; Rand, C. R.; Clark, T. P.; Landis, C. R.; Abboud, K. A. Org. Lett. 2007, 9, 2665.
[29] McDonald, R. I.; Wong, G. W.; Neupane, R. P.; Stahl, S. S.; Landis, C. R. J. Am. Chem. Soc. 2010, 132, 14027.
[30] Watkins, A. L.; Hashiguchi, B. G.; Landis, C. L. Org. Lett. 2008, 10, 4553.
[31] Clemens, A. J. L.; Burke, S. D. J. Org. Chem. 2012, 77, 2983.
[32] Risi, R. M.; Burke, S. D. Org. Lett. 2012, 14, 1180.
[33] Axtell, A. T.; Cobley, C. J.; Klosin, J.; Whiteker, G. T.; Zanotti-Gerosa, A.; Abboud, K. A. Angew. Chem., Int. Ed. 2005, 44, 5834.
[34] Zhang, Z.; Qian, H.; Longmire, J.; Zhang, X. J. Org. Chem. 2000, 65, 6223.
[35] Sherill, W. M.; Rubin, M. J. Am. Chem. Soc. 2008, 130, 13804.
[36] Tamura, K.; Sugiya, M.; Yoshida, K.; Yanagisawa, K.; Imamoto, T. Org. Lett. 2010, 12, 4400.
[37] (a) Wang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2011, 133, 19080. (b) Uhlemann, M.; Börner, A. ChemCatChem 2012, 4, 753.
[38] (a) Keuelemans, A. I. M.; Kwantes, A.; van Bavel, T. Recl. Trav. Chim. Pays-Bas 1948, 67, 298. (b) Clarke, M. L.; Roff, G. J. Chem.-Eur. J. 2006, 12, 7978.
[39] (a) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029. (b) Xie, J.-H.; Zhu, S.-F.; Zhou, Q.-L. Chem. Rev. 2011, 111, 1713. (c) Wang, D.-S.; Chen, Q.-A.; Lu, S.-M.; Zhou, Y.-G. Chem. Rev. 2012, 112, 2557. (d) Guo, H.; Ding, K.; Dai, L. Chin. Sci. Bull. 2004, 49, 1575 (in Chinese). (郭红超, 丁奎岭, 戴立信, 科学通报, 2004, 49, 1575.) (e) Xie, J.-H.; Zhu, S.-F.; Zhou, Q.-L. Acta Chim. Sinica 2012, 70, 1427. (f) Liu, Y.; Wang, Z.; Ding, K. Acta Chim. Sinica 2012, 70, 1427.
[40] (a) Mazuela, J.; Pàmies, O.; Diéguez, M.; Palais, L.; Rosset, S.; Alexakis, A. Tetrahedron: Asymmetry 2010, 21,2153. (b) Carrilho, R. M. B.; Neves, A. C. B.; Lourenco, M. A. O.; Abreu, A. R.; Rosado, M. T. S.; Abreu, P. E.; Eusébio, M. E. S.; Kollár, L.; Bayón, J. C.; Pereira, M. M. J. Organomet. Chem. 2012, 698, 28. (c) Fan, B.-M.; Xie, J.-H.; Zhou, Z.-T.; Zang, Q.; Tu, Y.-Q.; Zhou, Q.-L. Chem. J. Chin. Univ. 2006, 27, 1984 (in Chinese). (樊保敏, 谢建华, 周章涛, 张齐, 涂永强, 周其林, 高等学校化学学报, 2006, 27, 1984.)
[41] Hua, Z.; Vassar, V. C.; Choi, H.; Ojima, I. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 5411.
[42] Li, Y.; Wang, Z.; He, Y.; Fan, Q. Chin. J. Org. Chem. 2010, 30, 338 (in Chinese). (李永，王志玲，何艳梅，范青华，有机化学, 2010, 30, 338.)
[43] Kuil, M.; Goudriaan, P. E.; van Leeuwen, P. W. N. M.; Reek, J. N. H. Chem. Commun. 2006, 4679.
[44] Bellini, R.; Reek, J. N. H. Chem. Eur. J. 2012, 18, 13510.
[45] Gadzikwa, T.; Bellini, R.; Dekker, H. L.; Reek, J. N. H. J. Am. Chem. Soc. 2012, 134, 2860.
[46] Breit, B.; Breuninger, D. J. Am. Chem. Soc. 2004, 126, 10244.
[47] Worthy, A. D.; Joe, C. L.; Lightburn, T. E.; Tan, K. L. J. Am. Chem. Soc. 2010, 132, 14757.
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