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Metal—Organic Frameworks in Asymmetric Catalysis: Recent Advances

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Abstract

The review summarizes recent advances in the use of homochiral metal—organic frameworks (MOFs) in asymmetric catalysis of organic reactions.

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References

  1. Mikami, K. and Lautens, M., New Frontiers in Asymmetric Catalysis, Weinheim: Wiley, 2007.

    Book  Google Scholar 

  2. Maltsev, O.V., Beletskaya, I.P., and Zlotin, S.G., Russ. Chem. Rev., 2011, vol. 80, p. 1067. doi https://doi.org/10.1070/RC2011v080n11ABEH004249

    Article  CAS  Google Scholar 

  3. Pavlov, V.A. and Pavlova, T.N., Russ. Chem. Rev., 2012, vol. 81, p. 823. doi https://doi.org/10.1070/RC2012v081n09ABEH004305

    Article  CAS  Google Scholar 

  4. Beletskaya, I.P. and Averin, A.D., Curr. Organocatal., 2016, vol. 3, p. 60. doi https://doi.org/10.2174/2213337202666150505230013

    Article  CAS  Google Scholar 

  5. Beletskaya, I.P., Nájera, C., and Yus, M., Chem. Rev., 2018, vol. 118, p. 5080. doi https://doi.org/10.1021/acs.chemrev.7b00561

    Article  CAS  PubMed  Google Scholar 

  6. Anokhin, M.V., Feofanov, M.N., Averin, A.D., and Beletskaya, I.P., ChemistrySelect, 2018, vol. 3, p. 1388. doi https://doi.org/10.1002/slct.201703028

    Article  CAS  Google Scholar 

  7. Klabunovskii, E.I., Katal. Prom-sti., 2005, p. 3.

  8. Blaser, H.-U. and Federsel, H.-J., Asymmetric Catalysis on Industrial Scale: Challenges, Approaches, and Solutions, Weinheim: Wiley, 2010, 2nd ed.

    Book  Google Scholar 

  9. Yutkin, M.P., Dybtsev, D.N., and Fedin, V.P., Russ. Chem. Rev., 2011, vol. 80, p. 1009. doi https://doi.org/10.1070/RC2011v080n11ABEH004193

    Article  CAS  Google Scholar 

  10. Corma, A., García, H., and Llabrés i Xamena, F.X., Chem. Rev., 2010, vol. 110, p. 4606. doi https://doi.org/10.1021/cr9003924

    Article  CAS  PubMed  Google Scholar 

  11. Xu, W., Thapa, K.B., Ju, Q., Fang, Z., and Huang, W., Coord. Chem. Rev., 2018, vol. 373, p. 199. doi https://doi.org/10.1016/j.ccr.2017.10.014

    Article  CAS  Google Scholar 

  12. Yang, D. and Gates, B.C., ACS Catal., 2019, vol. 9, p. 1779. doi https://doi.org/10.1021/acscatal.8b04515

    Article  CAS  Google Scholar 

  13. Ma, L., Abney, C., and Lin, W., Chem. Soc. Rev., 2009, vol. 38, p. 1248. doi https://doi.org/10.1039/B807083K

    Article  CAS  PubMed  Google Scholar 

  14. Wang, C., Zheng, M., and Lin, W., J. Phys. Chem. Lett., 2011, vol. 2, p. 1701. doi https://doi.org/10.1021/jz200492d

    Article  CAS  Google Scholar 

  15. Leus, K., Liu, Y.-Y., and Van Der Voort, P., Catal. Rev.: Sci. Eng., 2014, vol. 56, p. 1. doi https://doi.org/10.1080/01614940.2014.864145

    Article  CAS  Google Scholar 

  16. Chughtai, A.H., Ahmad, N., Younus, H.A., Laypkov, A., and Verpoort, F., Chem. Soc. Rev., 2015, vol. 44, p. 6804. doi https://doi.org/10.1039/C4CS00395K

    Article  CAS  PubMed  Google Scholar 

  17. Gheorghe, A., Tepaske, M.A., and Tanase, S., Inorg. Chem. Front., 2018, vol. 5, p. 1512. doi https://doi.org/10.1039/C8QI00063H

    Article  CAS  Google Scholar 

  18. Wen, Y., Zhang, J., Xu, Q., Wu, X.-T., and Zhu, Q.-L., Coord. Chem. Rev., 2018, vol. 376, p. 248. doi https://doi.org/10.1016/j.ccr.2018.08.012

    Article  CAS  Google Scholar 

  19. Bhattacharjee, S., Khan, M.I., Li, X., Zhu, Q.-L., and Wu, X.-T., Catalysts, 2018, vol. 8, p. 120. doi https://doi.org/10.3390/catal8030120

    Article  CAS  Google Scholar 

  20. Seo, J.S., Whang, D., Lee, H., Jun, S.I., Oh, J., Jeon, Y.J., and Kim, K., Nature, 2000, vol. 404, p. 982. doi https://doi.org/10.1038/35010088

    Article  CAS  PubMed  Google Scholar 

  21. Falkowski, J.M., Sawano, T., Zhang, T., Tsun, G., Chen, Y., Lockard, J.V., and Lin, W., J. Am. Chem. Soc., 2014, vol. 136, p. 5213. doi https://doi.org/10.1021/ja500090y

    Article  CAS  PubMed  Google Scholar 

  22. Sawano, T., Ji, P., McIsaac, A.R., Lin, Z., Abney, C.W., and Lin, W., Chem. Sci., 2015, vol. 6, p. 7163. doi https://doi.org/10.1039/C5SC02100F

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  23. Nguyen, K.D., Kutzscher, C., Drache, F., Senkovska, I., and Kaskel, S., Inorg. Chem., 2018, vol. 57, p. 1483. doi https://doi.org/10.1021/acs.inorgchem.7b02854

    Article  CAS  PubMed  Google Scholar 

  24. Han, Q., He, C., Zhao, M., Qi, B., Niu, J., and Duan, C., J. Am. Chem. Soc., 2013, vol. 135, p. 10186. doi https://doi.org/10.1021/ja401758c

    Article  CAS  PubMed  Google Scholar 

  25. Han, Q., Qi, B., Ren, W., He, C. Niu, J., and Duan, C., Nat. Commun., 2015, vol. 6, p. 10007. doi https://doi.org/10.1038/ncomms10007

    Article  CAS  PubMed  Google Scholar 

  26. Xia, Q., Li, Z., Tan, C., Liu, Y., Gong, W., and Cui, Y., J. Am. Chem. Soc., 2017, vol. 139, p. 8259. doi https://doi.org/10.1021/jacs.7b03113

    Article  CAS  PubMed  Google Scholar 

  27. Li, Z., Liu, Y., Xia, Q., and Cui, Y., Chem. Commun., 2017, vol. 53, p. 12313. doi https://doi.org/10.1039/C7CC06979K

    Article  CAS  Google Scholar 

  28. Xi, W., Liu, Y., Xia, Q., Li, Z., and Cui, Y., Chem. Eur. J., 2015, vol. 21, p. 12581. doi https://doi.org/10.1002/chem.201501486

    Article  CAS  PubMed  Google Scholar 

  29. Zhu, C., Xia, Q., Chen, X., Liu, Y., Du, X., and Cui, Y., ACS Catal., 2016, vol. 6, p. 7590. doi https://doi.org/10.1021/acscatal.6b02359

    Article  CAS  Google Scholar 

  30. Du, X., Li, Z., Liu, Y., Yang, S., and Cui, Y., Dalton Trans., 2015, vol. 44, p. 12999. doi https://doi.org/10.1039/C5DT01682G

    Article  CAS  PubMed  Google Scholar 

  31. Li, J., Ren, Y., Qia, C., and Jiang, H., Chem. Commun., 2017, vol. 53, p. 8223. doi https://doi.org/10.1039/C7CC03499G

    Article  CAS  Google Scholar 

  32. Mo, K., Yang, Y., and Cui, Y., J. Am. Chem. Soc., 2014, vol. 136, p. 1746. doi https://doi.org/10.1021/ja411887c

    Article  CAS  PubMed  Google Scholar 

  33. Li, Z., Liu, Y., Kang, X., and Cui, Y., Inorg. Chem., 2018, vol. 57, p. 9786. doi https://doi.org/10.1021/acs.inorgchem.8b01630

    Article  CAS  PubMed  Google Scholar 

  34. Bonnefoy, J., Legrand, A., Quadrelli, E.A., Canivet, J., and Farrusseng, D., J. Am. Chem. Soc., 2015, vol. 137, p. 9409. doi https://doi.org/10.1021/jacs5b05327

    Article  CAS  PubMed  Google Scholar 

  35. Serra-Crespo, P., Ramos-Fernandez, E.V., Gascon, J., and Kapteijn, F., Chem. Mater., 2011, vol. 23, p. 2565. doi https://doi.org/10.1021/cm103644b

    Article  CAS  Google Scholar 

  36. Liu, L., Zhou, T.-Y., and Telfer, S.G., J. Am. Chem. Soc., 2017, vol. 139, p. 13936. doi https://doi.org/10.1021/jacs.5b05327

    Article  CAS  PubMed  Google Scholar 

  37. Zhu, W., He, C., Wu, P., Wu, X., and Duan, C., Dalton Trans., 2012, vol. 41, p. 3072. doi https://doi.org/10.1039/C2DT12153K

    Article  CAS  PubMed  Google Scholar 

  38. Liu, Y., Xi, X., Ye, C., Gong, T., Yang, Z., and Cui, Y., Angew. Chem., Int. Ed., 2014, vol. 53, p. 13821. doi https://doi.org/10.1002/anie.201408896

    Article  CAS  Google Scholar 

  39. Kutzscher, C., Nickerl, G., Senkovska, I., Bon, V., and Kaskel, S., Chem. Mater., 2016, vol. 28, p. 2573. doi https://doi.org/10.1021/acs.chemmater.5b04575

    Article  CAS  Google Scholar 

  40. Dong, X.-W., Yang, Y., Che, J.-X., Zuo, J., Li, X.-H., Gao, L., Hua, Y.-Z., and Liu, X.-Y., Green Chem., 2018, vol. 20, p. 4085. doi https://doi.org/10.1039/C8GC01323C

    Article  CAS  Google Scholar 

  41. Fan, Y., Ren, Y., Li, J., Yue, C., and Jiang, H., Inorg. Chem., 2018, vol. 57, p. 11986. doi https://doi.org/10.1021/acs.inorgchem.8b01551

    Article  CAS  PubMed  Google Scholar 

  42. Yu, Y.-H., Ye, H.-T., Hou, G.-F., Ren, C.-Y., Gao, J.-S., and Yan, P.-F., Cryst. Growth Des., 2016, vol. 16, p. 5669. doi https://doi.org/10.1021/acs.cgd.6b00593

    Article  CAS  Google Scholar 

  43. Hu, Y.-H., Liu, C.-X., Wang, J.-C., Ren, X.-H., Kan, X., and Dong, Y.-B., Inorg. Chem., 2019, vol. 58, p. 4722. doi https://doi.org/10.1021/acs.inorgchem.8b02132

    Article  CAS  PubMed  Google Scholar 

  44. Jeong, K.S., Go, Y.B., Shin, S.M., Lee, S.J., Kim, J., Yaghi, O.M., and Jeong, N., Chem. Sci., 2011, vol. 2, p. 877. doi https://doi.org/10.1039/C0SC00582G

    Article  CAS  Google Scholar 

  45. Lee, M., Shin, S.M., Jeong, N., and Thallapally, P.K., Dalton Trans., 2015, vol. 44, p. 9349. doi https://doi.org/10.1039/C5DT01322D

    Article  CAS  PubMed  Google Scholar 

  46. Lee, M.S., Shin, S.M., Kim, H.J., and Jeong, N., Bull. Korean Chem. Soc., 2015, vol. 36, p. 1282. doi https://doi.org/10.1002/bkcs.10228

    Article  CAS  Google Scholar 

  47. Tanaka, K., Nagase, S., Anami, T., Wierzbicki, M., and Urbanczyk-Lipkowska, Z., RSC Adv., 2016, vol. 6, p. 111 436. doi https://doi.org/10.1039/C6RA23740A

    Article  CAS  Google Scholar 

  48. Xia, Q., Liu, Y., Li, Z., Gong, W., and Cui, Y., Chem. Commun., 2016, vol. 52, p. 13 167. doi https://doi.org/10.1039/C6CC06019F

    Article  CAS  Google Scholar 

  49. Sawano, T., Thacker, N.C., Lin, Z., McIsaac, A.R., and Lin, W., J. Am. Chem. Soc., 2015, vol. 137, p. 12241. doi https://doi.org/10.1021/jacs.5b09225

    Article  CAS  PubMed  Google Scholar 

  50. Dybtsev, D.N., Nuzhdin, A.L., Chun, H., Bryliakov, K.P., Talsi, E.P., Fedin, V.P., and Kim, K., Angew. Chem., Int. Ed., 2006, vol. 45, p. 916. doi https://doi.org/10.1002/anie.200503023

    Article  CAS  Google Scholar 

  51. Dybtsev, D.N., Yutkin, M.P., Samsonenko, D.G., Fedin, V.P., Nuzhdin, A.L., Bezrukov, A.A., Bryliakov, K.P., Talsi, E.P., Belosludov, R.V., Mizuseki, H., Kawazoe, Y., Subbotin, O.S., and Belosludov, V.R., Chem. Eur. J., 2010, vol. 16, p. 10 348. doi https://doi.org/10.1002/chem.201000522

    Article  CAS  Google Scholar 

  52. Nuzhdin, A.L., Dybtsev, D.N., Bryliakov, K.P., Talsi, E.P., and Fedin, V.P., J. Am. Chem. Soc., 2007, vol. 129, p. 12958. doi https://doi.org/10.1021/ja076276p.54

    Article  CAS  PubMed  Google Scholar 

  53. Li, J., Ren, Y., Yue, C., Fan, Y., Qi, C., and Jiang, H., ACS Appl. Mater. Interfaces, 2018, vol. 10, p. 36047. doi https://doi.org/10.1021/acsami.8b14118

    Article  CAS  PubMed  Google Scholar 

  54. Chen, J., Chen, X., Zhang, Z., Bao, Z., Xing, H., Yang, Q., and Ren, Q., Mol. Catal., 2018, vol. 445, p. 163. doi https://doi.org/10.1016/j.mcat.2017.11.012

    Article  CAS  Google Scholar 

  55. Zheng, M., Liu, Y., Wang, C., Liu, S., and Lin, W., Chem. Sci., 2012, vol. 3, p. 2623. doi https://doi.org/10.1039/C2SC20379K

    Article  CAS  Google Scholar 

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Funding

The review was prepared under support by basic budgetary financing.

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Authors and Affiliations

  1. Nikolaev Institute of Inorganic Chemistry, Siberian Branch, Russian Academy of Sciences, Novosibirsk, Russia

    A. V. Artem’ev & V. P. Fedin

  2. Novosibirsk State University, Novosibirsk, Russia

    A. V. Artem’ev & V. P. Fedin

Authors
  1. A. V. Artem’ev
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  2. V. P. Fedin
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Corresponding author

Correspondence to V. P. Fedin.

Additional information

Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 6, pp. 901–922.

Conflict of Interests

The authors declare the absence of conflict of interests.

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Artem’ev, A.V., Fedin, V.P. Metal—Organic Frameworks in Asymmetric Catalysis: Recent Advances. Russ J Org Chem 55, 800–817 (2019). https://doi.org/10.1134/S1070428019060101

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