Citation: Huang Jiapian, Gu Qing, You Shuli. Synthesis of Planar Chiral Ferrocenes via Transition-Metal-Catalyzed Direct C-H Bond Functionalization[J]. Chinese Journal of Organic Chemistry, ;2018, 38(1): 51-61. doi: 10.6023/cjoc201708030 shu

Synthesis of Planar Chiral Ferrocenes via Transition-Metal-Catalyzed Direct C-H Bond Functionalization

  • Corresponding author: Gu Qing, qinggu@sioc.ac.cn You Shuli, slyou@sioc.ac.cn
  • Received Date: 15 August 2017
    Revised Date: 13 September 2017
    Available Online: 15 January 2017

    Fund Project: the National Natural Science Foundation of China 21572250Project supported by the National Key R&D Program of China (No. 2016YFA0202900), the National Basic Research Program of China (973 Program, No. 2015CB856600), the National Natural Science Foundation of China (Nos. 21332009, 21421091, 21572250), and the Chinese Academy Sciences (Nos. XDB20000000, QYZDY-SSW-SLH012)the National Basic Research Program of China 2015CB856600the Chinese Academy Sciences XDB20000000the National Key R&D Program of China 2016YFA0202900the Chinese Academy Sciences QYZDY-SSW-SLH012the National Basic Research Program of China 973 Programthe National Natural Science Foundation of China 21421091the National Natural Science Foundation of China 21332009

Figures(22)

  • Ferrocenes bearing planar chirality have been demonstrated to be highly efficient ligands or catalysts in asymmetric catalysis. In view of their atom and step economies, direct asymmetric C—H bond functionalization is the most concise and powerful method for the construction of planar chiral ferrocenes compared with traditional approaches. This review summarizes recent progress on the development of novel methods to synthesize planar chiral compounds via transition-metal (Cu-, Pd-, Ir-, Rh-, Au-, Pt-) catalyzed asymmetric C—H bond functionalization. Preparation of a variety of new planar chiral ferrocene-based catalysts and ligands by utilizing these methods and their application in catalytic asymmetric reactions are also discussed.
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    1. [1]

      (a) Hayashi, T.; Togni, A. Ferrocenes, VCH, Weinheim, Germany, 1995.
      (b) Togni, A.; Haltermann, R. L. Metallocenes, VCH, Weinheim, Germany, 1998.
      (c) Štěpnička, P. Ferrocenes, Wiley, Chichester, 2008.
      (d) Dai, L.-X.; Hou, X.-L. Chiral Ferrocenes in Asymmetric Catalysis, Wiley, Weinheim, 2010.

    2. [2]

    3. [3]

      (a) Blaser, H.-U.; Brieden, W.; Pugin, B.; Spindler, F.; Studer, M.; Togni, A. Top. Catal. 2002, 19, 3.
      (b) Blaser, H.-U.; Pugin, B.; Spindler, F. J. Mol. Catal. A 2005, 231, 1.

    4. [4]

      (a) Battelle, L. F.; Bau, R.; Gokel, G. W.; Oyakawa, R. T.; Ugi, I. K. J. Am. Chem. Soc. 1973, 95, 482.
      (b) Rebière, F.; Riant, O.; Ricard, L.; Kagan, H. B. Angew. Chem., Int. Ed. 1993, 32, 568.
      (c) Richards, C. J.; Damalidis, T.; Hibbs, D. E.; Hursthouse, M. B. Synlett 1995, 74.
      (d) Tsukazaki, M.; Tinkl, M.; Roglans, A.; Chapell, B. J.; Taylor, N. J.; Snieckus, V. J. Am. Chem. Soc. 1996, 118, 685.
      (e) Enders, D.; Peters, R.; Lochtman, R.; Raabe, G. Angew. Chem., Int. Ed. 1999, 38, 2421.
      (f) Laufer, R. S.; Veith, U.; Taylor, N. J.; Snieckus, V. Org. Lett. 2000, 2, 629.
      (g) Bolm, C.; Kesselgruber, M.; Muñiz, K.; Raabe, G. Organometallics 2000, 19, 1648.
      (h) Bolm, C.; Kesselgruber, M.; Raabe, G. Organometallics 2002, 21, 707.
      (i) Genet, C.; Canipa, S. J.; O'Brein, P.; Taylor, S. J. Am. Chem. Soc. 2006, 128, 9336.
      For a review on kinetic resolution:(j) Alba, A.-N.; Rios, R. Molecules 2009, 14, 4747.
      (k) Mercier, A.; Yeo, W. C.; Chou, J.; Chaudhuri, P. D.; Bernardinelli, G.; Kündig, E. P. Chem. Commun. 2009, 5227.
      (l) Mercier, A.; Urbaneja, X.; Yeo, W. C.; Chaudhuri, P. D.; Cumming, G. R.; House, D.; Bernardinelli, G.; Kündig, E. P. Chem.-Eur. J. 2010, 16, 6285.
      (m) Ogasawara, M.; Arae, S.; Watanabe, S.; Nakajima, K.; Takahashi, T. Chem.-Eur. J. 2013, 19, 4151.

    5. [5]

      For reviews and book, see:
      (a) Giri, R.; Shi, B.-F.; Engle, K. M.; Maugel, N.; Yu, J.-Q. Chem. Soc. Rev. 2009, 38, 3242.
      (b) Peng, H. M.; Dai, L.-X.; You, S.-L. Angew. Chem., Int. Ed. 2010, 49, 5826.
      (c) Wencel-Delord, J.; Colobert, F. Chem.-Eur. J. 2013, 19, 14010.
      (d) Engle, K. M.; Yu, J.-Q. J. Org. Chem. 2013, 78, 8927.
      (e) Zheng, C.; You, S.-L. RSC Adv. 2014, 4, 6173.
      (f) Ye, B.; Cramer, N. Acc. Chem. Res. 2015, 48, 1308.
      (g) You, S.-L. Asymmetric Functionalization of C-H Bonds, RSC, Cambridge, U.K., 2015.
      (h) Gao, D.-W.; Gu, Q.; Zheng, C.; You, S.-L. Acc. Chem. Res. 2017, 50, 351.
      (i) Newton, C. G.; Wang, S.-G.; Oliveira, C. C.; Cramer, N. Chem. Rev. 2017, 117, 8908.

    6. [6]

    7. [7]

      Xia, J.-B.; You, S.-L. Organometallics 2007, 26, 4869.  doi: 10.1021/om700806e

    8. [8]

      Takebayashi, S.; Shizuno, T.; Otani, T.; Shibata, T. Beilstein J. Org. Chem. 2012, 8, 1844.  doi: 10.3762/bjoc.8.212

    9. [9]

      Siegel, S.; Schmalz, H.-G. Angew. Chem., Int. Ed. 1997, 36, 2456.  doi: 10.1002/(ISSN)1521-3773

    10. [10]

      (a) Sokolov, V. I.; Troitskaya, L. L. Chimia 1978, 32, 122.
      (b) Sokolov, V. I.; Troitskaya, L. L.; Reutov, O. A. J. Organomet. Chem. 1979, 182, 537.
      (c) Günay, M. E.; Richards, C. J. Organometallics 2009, 28, 5833.

    11. [11]

      (a) Shi, B.-F.; Maugel, N.; Zhang, Y.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2008, 47, 4882.
      (b) Shi, B.-F.; Zhang, Y.-H.; Lam, J. K.; Wang, D.-H.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 460.
      (c) Wasa, M.; Engle, K. M.; Lin, D. W.; Yoo, E. J.; Yu, J.-Q. J. Am. Chem. Soc. 2011, 133, 19598.
      (d) Musaev, D. G.; Kaledin, A.; Shi, B.-F.; Yu, J.-Q. J. Am. Chem. Soc. 2012, 134, 1690.
      (e) Xiao, K.-J.; Lin, D. W.; Miura, M.; Zhu, R.-Y.; Gong, W.; Wasa, M.; Yu, J.-Q. J. Am. Chem. Soc. 2014, 136, 8138.
      (f) Chu, L.; Xiao, K.-J.; Yu, J.-Q. Science 2014, 346, 451.
      (g) Chan, K. S. L.; Fu, H.-Y.; Yu, J.-Q. J. Am. Chem. Soc. 2015, 137, 2042.
      (h) Laforteza, B. N.; Chan, K. S. L.; Yu, J.-Q. Angew. Chem., Int. Ed. 2015, 54, 11143.
      (i) Xiao, K.-J.; Chu, L.; Yu, J.-Q. Angew. Chem., Int. Ed. 2016, 55, 2856.
      (j) Xiao, K.-J.; Chu, L.; Chen, G.; Yu, J.-Q. J. Am. Chem. Soc. 2016, 138, 7796.

    12. [12]

      Gao, D.-W.; Shi, Y.-C.; Gu, Q.; Zhao, Z.-L.; You, S.-L. J. Am. Chem. Soc. 2013, 135, 86.  doi: 10.1021/ja311082u

    13. [13]

      Cheng, G.-J.; Chen, P.; Sun, T.-Y.; Zhang, X.; Yu, J.-Q.; Wu, Y.-D. Chem. Eur. J. 2015, 21, 11180.  doi: 10.1002/chem.v21.31

    14. [14]

      Gair, J.-J.; Haines, B.-E.; Filatov, A.-S.; Musaev, D.-G.; Lewis, J.-C. Chem. Sci. 2017, 8, 5746.  doi: 10.1039/C7SC01674C

    15. [15]

      Pi, C.; Li, Y.; Cui, X.-L.; Zhang, H.; Han, Y.-B.; Wu, Y.-J. Chem. Sci. 2013, 4, 2675.  doi: 10.1039/c3sc50577d

    16. [16]

      Shi, Y.-C.; Yang, R.-F.; Gao, D.-W.; You, S.-L. Beilstein J. Org. Chem. 2013, 9, 1891.  doi: 10.3762/bjoc.9.222

    17. [17]

      Zhang, H.; Cui, X.-L.; Yao, X.-Y.; Wang, H.; Zhang, J.-Y.; Wu, Y.-J. Org. Lett. 2012, 14, 3012.  doi: 10.1021/ol301063k

    18. [18]

      Gao, D.-W.; Gu, Q.; You, S.-L. J. Am. Chem. Soc. 2016, 138, 2544.  doi: 10.1021/jacs.6b00127

    19. [19]

      Pi, C.; Cui, X.-L.; Liu, X.-Y.; Guo, M.X.; Zhang, H.-Y.; Wu, Y.-J. Org. Lett. 2014, 16, 5164.  doi: 10.1021/ol502509f

    20. [20]

      Gao, D.-W.; Yin, Q.; Gu, Q.; You, S.-L. J. Am. Chem. Soc. 2014, 136, 4841.  doi: 10.1021/ja500444v

    21. [21]

      Fukuzawa, S.-I.; Yamamoto, M.; Hosaka, M.; Kikuchi, S. Eur. J. Org. Chem. 2007, 5540.
       

    22. [22]

      Deng, R.; Huang, Y.; Ma, X.; Li, G.; Zhu, R.; Wang, B.; Kang, Y.-B.; Gu, Z. J. Am. Chem. Soc. 2014, 136, 4472.  doi: 10.1021/ja500699x

    23. [23]

      Zhang, S.; Lu, J.; Ye, J.; Duan, W.-L. Chin. J. Org. Chem. 2016, 36, 752(in Chinese).
       

    24. [24]

      (a) Nottingham, C.; Müller-Bunz, H.; Guiry, P. J. Angew. Chem., Int. Ed. 2016, 55, 11115.
      (b) Nottingham, C.; Müller-Bunz, H.; McGlinchey, M. J.; Guiry, P. J. Eur. J. Org. Chem. 2017, 2848.

    25. [25]

      (a) Ma, X.; Gu, Z. RSC. Adv. 2014, 4, 36241.
      (b) Liu, L.; Zhang, A.-A.; Zhao, R.-J.; Li, F.; Meng, T.-J.; Ishida, N.; Murakami, M.; Zhao, W.-X. Org. Lett. 2014, 16, 5336.

    26. [26]

      Gao, D.-W.; Zheng, C.; Gu, Q.; You, S.-L. Organometallics 2015, 34, 4618.  doi: 10.1021/acs.organomet.5b00730

    27. [27]

      Gao, D.-W.; Gu, Y.; Wang, S.-B.; Gu, Q.; You, S.-L. Organometallics 2016, 35, 3227.  doi: 10.1021/acs.organomet.6b00569

    28. [28]

      (a) Shibata, T.; Shizuno, T. Angew. Chem., Int. Ed. 2014, 53, 5410.
      (b) Takebayashi, S.; Shibata, T. Organometallics 2012, 31, 4114.

    29. [29]

      (a) Shibata, T.; Shizuno, T.; Sasaki, T. Chem. Commun. 2015, 51, 7802.
      (b) Zhang, Q.-W.; An, K.; Liu, L.-C.; Yue, Y.; He, W. Angew. Chem., Int. Ed. 2015, 54, 6918.
      (c) Murai, M.; Matsumoto, K.; Takeuchi, Y.; Takai, K. Org. Lett. 2015, 17, 3102.

    30. [30]

      Wang, S.-B.; Zheng, J.; You, S.-L. Organometallics 2016, 35, 1420.  doi: 10.1021/acs.organomet.6b00020

    31. [31]

      Guimond, N.; Gouliaras, C.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 6908.  doi: 10.1021/ja102571b

    32. [32]

      Urbano, A.; Hernández-Torres, G.; del Hoyo, A. M.; Martínez-Carrión, A.; Carre o, M. C. Chem. Commun. 2016, 52, 6419.  doi: 10.1039/C6CC02624A

    33. [33]

      Shibata, T.; Uno, N.; Sasaki, T.; Kanyiva, K. S. J. Org. Chem. 2016, 81, 6266.  doi: 10.1021/acs.joc.6b00825

    34. [34]

      Fürstner, A.; Mamane, V. J. Org. Chem. 2002, 67, 6264.  doi: 10.1021/jo025962y

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