Citation: Gao Anli, Ye Qingsong, Yu Juan, Liu Weiping. Research Advances of the Chiral Binap-Ru (Ⅱ) Catalysts in Asymmetric Hydrogenation Reactions[J]. Chinese Journal of Organic Chemistry, ;2017, 37(1): 47-78. doi: 10.6023/cjoc201606024 shu

Research Advances of the Chiral Binap-Ru (Ⅱ) Catalysts in Asymmetric Hydrogenation Reactions

  • Corresponding author: Liu Weiping, liuweiping0917@126.com
  • Received Date: 14 June 2016
    Revised Date: 12 August 2016

    Fund Project: the Yunnan Province Scientific Creative Plan 2015AA006the 12th National Scientific Support Plan 2012BAE06B08the Yunnan Province Scientific Creative Plan 2013B019

Figures(26)

  • Chiral 2, 2'-bis (diphenylphosphino)-1, 1'-binapthyl (Binap) ligand consists of a pair of 2-diphenylphosphinonaphthyl groups connected at the 1 and 1'positions, being of the nature of the C2-axial chirality with optical activity of ±234°.The Binap can coordinate with many transitional metals to form stable chelation complexes, effecting the chirality transfer to the metal center for function in asymmetrically catalytic reactions.This contribution is focused on the Binap-Ru (Ⅱ) catalytic system that covers the various substrates, reaction conditions, enantioselectivity of the products, reaction mechanism, and others on the basis of the prepared stable Binap-Ru (Ⅱ) complexes as the clue in the text.This study will give a deep understanding of this system especially concerning the applied catalytic synthesis of the useful organic molecules.
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    1. [1]

      Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932.  doi: 10.1021/ja00547a020

    2. [2]

      Ikariya, T.; Ishii, Y.; Kawano, H.; Arai, T.; Saburi, M.; Yoshikawa, S.; Akutagawa, S. J. Chem. Soc., Chem. Commun. 1985, 922.

    3. [3]

      Noyori, R.; Ohta, M.; Hsiao, Y.; Kitamura, M.; Ohta, T.; Takaya, H. J. Am. Chem. Soc. 1986, 108, 7 117.  doi: 10.1021/ja00261a002

    4. [4]

      Kitamura, M.; Hsiao, Y.; Noyori, R. Takaya, H. Tetrahedron Lett. 1987, 28, 4829  doi: 10.1016/S0040-4039(00)96636-X

    5. [5]

      Kitamura, M.; Hsiao, Y.; Ohta, M.; Tsukamoto, M.; Ohta, T.; Takaya, H.; Noyori, R. J. Org. Chem. 1994, 59, 297.  doi: 10.1021/jo00081a007

    6. [6]

      Ohta, T.; Takaya, H.; Kitamura, M.; Nagai, K.; Noyori, R. J. Org. Chem. 1987, 52, 3174.  doi: 10.1021/jo00390a043

    7. [7]

      Takaya, H.; Ohta, T.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Inoue, S.; Kasahara, I.; Noyori, R. J. Am. Chem. Soc. 1987, 109, 1596.  doi: 10.1021/ja00239a065

    8. [8]

      Bernas, H.; Bernas, A.; Maki-Arvela, P.; Leino, R.; Murzin, Y. D. Catal. Sci. Technol. 2012, 2, 1901  doi: 10.1039/c2cy20249b

    9. [9]

      Kitamura, M.; Kasahara, I.; Manabe, K.; Noyori, R.; Takaya, H. J. Org. Chem. 1988, 53, 708..  doi: 10.1021/jo00238a048

    10. [10]

      Ashby, M. T.; Khan, M. A. Organometallics 1991, 10, 2011.  doi: 10.1021/om00052a057

    11. [11]

      Ashby, M. T.; Halpern, J. J. Am. Chem. Soc. 1991, 113, 589.  doi: 10.1021/ja00002a029

    12. [12]

      Manimaran, T.; Wu, T. C.; Klobucar, W. D.; Kolich, C. H.; Stahly, G. P. Organometallics 1993, 12, 1467.  doi: 10.1021/om00028a078

    13. [13]

      Chan, A. S.; Laneman, S. A.; Day, C. X. Inorg. Chim. Acta 1995, 228 159.  doi: 10.1016/0020-1693(94)04167-T

    14. [14]

      Chen, C. C.; Huang, T. T.; Lin, C. W.; Cao, R.; Chan, A. S. C.; Wong, W. T. Inorg. Chim. Acta 1988, 270, 247.

    15. [15]

      Ohta, T.; Miyake, T.; Seido, N.; Kumobayashi, H.; Takaya, H. J. Org. Chem. 1995, 60, 357.  doi: 10.1021/jo00107a014

    16. [16]

      Ohta, T.; Ikegami, H.; Miyake, T.; Takaya, H. J. Organomet. Chem. 1995, 502, 169.  doi: 10.1016/0022-328X(95)05819-B

    17. [17]

      Uemura, T.; Zhang, X. Y.; Matsumura, K.; Sayo, N.; Kumobayashi, H.; Ohta, T.; Nozaki, K.; Takaya, H. J. Org. Chem. 1996, 61, 5510.  doi: 10.1021/jo960426p

    18. [18]

      Marchetti, M.; Alberico, E.; Bertucci, C.; Botteghi, C.; Ponte, G. D. J. Mol. Catal. A:Chem. 1997, 125, 109.  doi: 10.1016/S1381-1169(97)00085-X

    19. [19]

      Shinohara, T.; Kondo, K.; Ogawa, H.; Mori, T.; Nozaki, K.; Hiyama, T. Chirality 2000, 12, 425.  doi: 10.1002/(ISSN)1520-636X

    20. [20]

      Kitamura, M.; Tsukamoto, M.; Bessho, Y.; Yoshimura, M.; Kobs, U.; Widhalm, M.; Noyori, R. J. Am. Chem. Soc. 2002, 124, 6649.  doi: 10.1021/ja010982n

    21. [21]

      Ciappa, A.; Matteoli, U.; Scrivanti, A. Tetrahedron:Asymmetry 2002, 13, 2193.  doi: 10.1016/S0957-4166(02)00538-4

    22. [22]

      Jessop, P. G.; Stanley, R. R.; Brown, R. A.; Eckert, C. A.; Liotta, C. L.; Ngo, T. T.; Pollet, P. Green Chem. 2003, 5, 123.  doi: 10.1039/b211894g

    23. [23]

      Dong, X., Erkey, C. J. Mol. Catal. A:Chem. 2004, 211, 73.  doi: 10.1016/j.molcata.2003.10.016

    24. [24]

      Yamano, T.; Yamashita, M.; Adachi, M.; Tanaka, M.; Matsumoto, K.; Kawada, M.; Uchikawa, O.; Fukatsu, K.; Ohkawa, S. Tetrahedron:Asymmetry 2006, 17, 184.  doi: 10.1016/j.tetasy.2005.11.005

    25. [25]

      Bisset, A. A.; Dishington, A.; Jones, T.; Clarkson, G. J.; Wills, M. Tetrahedron 2014, 70, 7207.  doi: 10.1016/j.tet.2014.06.046

    26. [26]

      Yoshimura, M.; Ishibashi, Y.; Miyata, K.; Bessho, Y.; Tsuka-moto, M.; Kitamura, M. Tetrahedron 2007, 63, 11399.  doi: 10.1016/j.tet.2007.08.071

    27. [27]

      Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144.  doi: 10.1021/ja00054a020

    28. [28]

      Doucet, H.; Gendre, P. L.; Bruneau, C.; Dixneuf, P. H.; Souvie, J. C. Tetrahedron:Asymmetry 1996, 7, 525  doi: 10.1016/0957-4166(96)00036-5

    29. [29]

      Tranchier, J. P.; Ratovelomanana-Vidal, V.; Genet, J. P.; Tong, S. J.; Cohen, T. Tetrahedron Lett. 1997, 38, 2951.  doi: 10.1016/S0040-4039(97)00530-3

    30. [30]

      Magnus, N. A.; Astleford, B. A.; Laird, D. L. T.; Maloney, T. D.; McFarland, A. D.; Rizzo, J. R.; Ruble, J. C.; Stephenson, G. A.; Wepsiec, J. P. J. Org. Chem. 2013, 78, 5768.  doi: 10.1021/jo400589j

    31. [31]

      Charette, A. B.; Glroux, A. Tetrahedron Lett. 1996, 37, 6669.  doi: 10.1016/S0040-4039(96)01471-2

    32. [32]

      Tomas-Mendivil, E.; Menendez-Rodriguez, L.; Francos, J.; Crochet, P.; Cadierno, V. RSC Adv. 2014, 4, 63466.  doi: 10.1039/C4RA12013B

    33. [33]

      Mashima, K.; Matsumura, Y.; Kusano, K, ; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Chem. Soc., Chem. Commun. 1991, 609.

    34. [34]

      Ohta, T.; Miyake, T.; Takaya, H. J. Chem. Soc., Chem. Commun. 1992, 1725.

    35. [35]

      Gelman, F.; Avnir, D.; Schumann, H.; Blum, J. J. Mol. Catal. A:Chem. 1999, 146, 123.  doi: 10.1016/S1381-1169(99)00103-X

    36. [36]

      Bronze-Uhle, E. S.; Sairre, M. I.; Donate, P. M.; Frederico, D. J. Mol. Catal. A:Chem. 2006, 259, 103  doi: 10.1016/j.molcata.2006.05.066

    37. [37]

      Mashima, K.; Kusano, K.; Sate, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064.  doi: 10.1021/jo00090a026

    38. [38]

      Schmidt, U.; Leitenberger, V.; Griesser, H.; Schmidt, J.; Meyer, R. Synthesis 1992, 1248.

    39. [39]

      Rane, V. H.; Tas, D.; Parton, R. F.; Jacobs, P. A. Catal. Lett. 1996, 41, 111.  doi: 10.1007/BF00811721

    40. [40]

      Bianchini, C.; Barbaro, P.; Scapacci, G.; Zanobini, F. Organometallics 2000, 19, 2450.  doi: 10.1021/om000137y

    41. [41]

      Wolfson, A, ; Vankelecom, I. F. J.; Geresh, S.; Jacobs, P. A. J. Mol. Catal. A:Chem. 2004, 217, 21.  doi: 10.1016/j.molcata.2004.03.014

    42. [42]

      Wolfson, A.; Vankelecom, I. F. J.; Jacobs, P. A. J. Organomet. Chem. 2005, 690, 3558.  doi: 10.1016/j.jorganchem.2005.03.017

    43. [43]

      Ahn, S. H.; Park, Y. H.; Jacobs, P. A. Surf. Sci. Catal. 2006, 159, 349.  doi: 10.1016/S0167-2991(06)81605-8

    44. [44]

      Jahjah, M.; Alame, M.; Pellet-Rostaing, S.; Lemaire, M. Tetrahedron:Asymmetry 2007, 18, 2305.  doi: 10.1016/j.tetasy.2007.09.022

    45. [45]

      Floris, T.; Kluson, P.; Bartek, L.; Pelantova, H. Appl. Catal. A:Gen. 2009, 366, 160.  doi: 10.1016/j.apcata.2009.07.002

    46. [46]

      Cerna, I.; Kluson, P.; Bendova, M.; Floris, T.; Pelantova, H.; Pekarek, T. Chem. Eng. Process. 2011, 50, 264.  doi: 10.1016/j.cep.2011.02.003

    47. [47]

      Theuerkauf, J.; Francio, G.; Leitner, W. Adv. Synth. Catal. 2013, 355, 209.  doi: 10.1002/adsc.201200724

    48. [48]

      Facchetti, S.; Jurcik, V.; Baldino, S.; Giboulot, S.; Nedden, H. G.; Zanotti-Gerosa, A.; Blackaby, A.; Bryan, R.; Boogaard, A.; McLaren, D. B.; Moya, E.; Reynolds, S.; Sandham, K. S.; Martinuzzi, P.; Baratta, W. Organometallics 2016, 35, 277.  doi: 10.1021/acs.organomet.5b00978

    49. [49]

      Kawano, H.; Ikariya, T.; Ishii, Y.; Saburi, M.; Yoshikawa, S.; Uchida, Y.; Kumobayashi, H. J. Chem. Soc., Perkin Trans. 1 1989, 1571.

    50. [50]

      Muramatsu, H.; Kawano, H.; Ishii, Y.; Saburi, M.; Uchida, Y. J. Chem. Soc., Chem. Commun. I989, 769.

    51. [51]

      Monteiro, A. L.; Zinn, F. K.; Souza, R. F.; Doupont, J. Tetrahe-dron:Asymmetry 1997, 8, 177.  doi: 10.1016/S0957-4166(96)00485-5

    52. [52]

      Yamamoto, T.; Ogura, M; Kanisawa, T. Tetrahedron 2002, 58, 9209.  doi: 10.1016/S0040-4020(02)01189-4

    53. [53]

      Kawano, H.; Ishii, Y.; Saburi, M.; Uchida, Y. J. Chem. Soc., Chem. Commun. 1988, 87.

    54. [54]

      Furstner, A.; Thiel, O. R.; Blanda, G. Org. Lett. 2000, 2, 3731.  doi: 10.1021/ol006646d

    55. [55]

      Furstner, A.; Dierkes, T.; Thiel, O. R.; Blanda, G. Chem. Eur. J. 2001, 7, 5286.  doi: 10.1002/(ISSN)1521-3765

    56. [56]

      Zhao, Z. Q.; Zhou, Z. Y.; Peng, L. Z. Chin. J. Pharm. 2006, 37, 726(in Chinese).

    57. [57]

      Kramer, R.; Bruckner, R. Angew. Chem., Int. Ed. 2007, 46, 6537.  doi: 10.1002/(ISSN)1521-3773

    58. [58]

      Kramer, R.; Bruckner, R. Chem. Eur. J. 2007, 13, 9076.  doi: 10.1002/(ISSN)1521-3765

    59. [59]

      Nair, D.; Wong, H. T.; Han, S. J.; Vankelecom, I. F. J.; White, L. S.; Livingston, A. G.; Boam, A. T. Org. Process Res. Dev. 2009, 13, 863.  doi: 10.1021/op900056s

    60. [60]

      Falkowski, J. M.; Sawano, T.; Zhang, T.; Tsun, G, ; Chen, Y.; Lockard, J. V.; Lin, W. B. J. Am. Chem. Soc. 2014, 136, 5213.  doi: 10.1021/ja500090y

    61. [61]

      Kitamura, M.; Ohkuma, T.; Takaya, H.; Noyori, R. Tetrahedron Lett. 1988, 29, 1555.  doi: 10.1016/S0040-4039(00)80350-0

    62. [62]

      Genet, J. P.; Ratovelomanana-Vidal, V.; Andrade, M. C.; Pfister, X.; Guerreiro, P.; Lenoir, J. Y. Tetrahedron Lett. 1995, 36, 4801.  doi: 10.1016/00404-0399(50)0873B-

    63. [63]

      Genet, J. P.; Andrade, M. C. C.; Ratovelomanana-Vidal, V. Tetrahedron Lett. 1995, 36, 2063.  doi: 10.1016/0040-4039(95)00182-C

    64. [64]

      Shioiri, T.; Terao, Y.; Irako, N.; Aoyama, T. Tetrahedron 1998, 54, 15701.  doi: 10.1016/S0040-4020(98)00984-3

    65. [65]

      Makino, K.; Goto, T.; Hiroki, Y.; Hamada, Y. Angew. Chem., Int. Ed. 2004, 43, 882.  doi: 10.1002/(ISSN)1521-3773

    66. [66]

      Huang, H. L.; Liu, L. T.; Chen, S. F.; Ku, H. Tetrahedron:Asymmetry 1998, 9, 1637  doi: 10.1016/S0957-4166(98)00158-X

    67. [67]

      Kitamura, M.; Ohkuma, T.; Tokunaga, M.; Noyori, R. Tetrahedron Asymmetry 1990, 1, 1.

    68. [68]

      Kitamura, M.; Okhuma, T.; Inoue, S.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629.  doi: 10.1021/ja00210a070

    69. [69]

      Kitamura, M.; Tokunaga, M.; Pham, T.; Lubell, W. D.; Noyori, R. Tetrahedron Lett. 1995, 36, 5769.  doi: 10.1016/00404-0399(50)11355-

    70. [70]

      Kitamura, M.; Yoshimura, M.; Kanda, N.; Noyori, R. Tetrahe-dron 1999, 55, 8769.  doi: 10.1016/S0040-4020(99)00443-3

    71. [71]

      Lamouille, T.; Saluzzo, C.; Halle, R.; Guyader, F. L.; Lemaire, M. Tetrahedron Lett. 2001, 42, 663.  doi: 10.1016/S0040-4039(00)02035-9

    72. [72]

      Berthod, M.; Saluzzo, C.; Mignani, G.; Lemaire, M. Tetrahedron:Asymmetry 2004, 15, 639.  doi: 10.1016/j.tetasy.2003.12.033

    73. [73]

      Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675.  doi: 10.1021/ja00114a043

    74. [74]

      Moreau, C.; Frost, C. G.; Murrer, B. Tetrahedron Lett. 1999, 40, 5617.  doi: 10.1016/S0040-4039(99)01044-8

    75. [75]

      Ohkuma, T.; Hattori, T.; Ooka, H.; Inoue, T.; Noyori, R. Org. Lett. 2004, 6, 2681.  doi: 10.1021/ol049157c

    76. [76]

      Liu, W. G.; Cui, X.; Cun, L. F.; Wu, J.; Zhu, J.; Deng, J. G.; Fan, Q. H. Synlett 2005, 1591.

    77. [77]

      Jing, Q.; Zhang, X.; Sun, J.; Ding, K. Adv. Synth. Catal. 2005, 347, 1193.  doi: 10.1002/(ISSN)1615-4169

    78. [78]

      Arai, N.; Azuma, K.; Nii, N.; Ohkuma, T. Angew. Chem., Int. Ed. 2008, 47, 7457.  doi: 10.1002/anie.v47:39

    79. [79]

      Ooka, H.; Arai, N.; Azuma, K.; Kurono, N.; Ohkuma, T. J. Org. Chem. 2008, 73, 9084.  doi: 10.1021/jo801863q

    80. [80]

      Arai, N.; Suzuki, K.; Sugizaki, S.; Sorimachi, H.; Ohkuma, T. Angew. Chem., Int. Ed. 2008, 47, 1770.  doi: 10.1002/(ISSN)1521-3773

    81. [81]

      Sandoval, C. A.; Li, Y. H.; Ding, K. L.; Noyori, R. Chem. Asian J. 2008, 3, 1801.  doi: 10.1002/asia.200800246

    82. [82]

      Chiwara, V. I.; Haraguchi, N.; Itsuno, S. J. Org. Chem. 2009, 74, 1391.  doi: 10.1021/jo802339t

    83. [83]

      Rivera, V. M.; Ruelas-Leyva, P. J.; Fuentes, G. A. Catal. Today 2013, 213, 109.  doi: 10.1016/j.cattod.2013.03.043

    84. [84]

      Arai, N.; Sato, K.; Azuma, K.; Ohkuma, T. Angew. Chem., Int. Ed. 2013, 52, 7500.  doi: 10.1002/anie.201303423

    85. [85]

      Boge, M.; Heck, J. Eur. J. Inorg. Chem. 2015, 2858.

    86. [86]

      Ohkuma, T.; Koizumi, M.; Muniz, K.; Hilt, G.; Kabuto, C.; Noyori, R. J. Am. Chem. Soc. 2002, 124, 6508.  doi: 10.1021/ja026136+

    87. [87]

      Sandoval, C. A.; Shi, Q. X.; Liu, S. S.; Noyori, R. Chem. Asian J. 2009, 4, 1221.  doi: 10.1002/asia.v4:8

    88. [88]

      Sandoval, C. A.; Ohkuma, T.; Muniz, K.; Noyori, R. J. Am. Chem. Soc. 2003, 125, 13490.  doi: 10.1021/ja030272c

    89. [89]

      Hamilton, R. J.; Bergens, S. H. J. Am. Chem. Soc. 2008, 130, 11979.  doi: 10.1021/ja8034812

    90. [90]

      Sui-Seng, S.; Hadzovic, A.; Lough, A. J.; Morris, R. H. Dalton Trans. 2007, 2536.

    91. [91]

      Takebayashi, S.; Bergens, S. H. Organometallics 2009, 28, 2349.  doi: 10.1021/om9002076

    92. [92]

      Takebayashi, S.; John, J. M.; Bergens, S. H. J. Am. Chem. Soc. 2010, 132, 12832.  doi: 10.1021/ja105783u

    93. [93]

      Matsumura, K.; Arai, N.; Hori, K.; Saito, T.; Sayo, N.; Ohkuma, T. J. Am. Chem. Soc. 2011, 133, 10696.  doi: 10.1021/ja202296w

    94. [94]

      Faza, O. N.; Fernandez, I.; Lopez, C. S. Chem. Commun. 2013, 49, 4277.  doi: 10.1039/C2CC37165K

    95. [95]

      Guo, R. W.; Lough, A. J.; Morris, R. H.; Song, D. T. Organometallics 2004, 23, 5524.  doi: 10.1021/om049460h

    96. [96]

      Abdur-Rashid, A.; Guo, R. W.; Lough, A. J.; Morris, R. H.; Song, D. T. Adv. Synth. Catal. 2005, 347, 571.  doi: 10.1002/(ISSN)1615-4169

    97. [97]

      Wiles, J. A.; Lee, C. E.; McDonald, R.; Bergens, S. H. Organometallics 1996, 15, 3782.  doi: 10.1021/om9603979

    98. [98]

      Noyori, R.; Ikeda, T.; Ohkuma, T.; Widhalm, M.; Kitamura, M.; Takaya, H.; Akutagawa, S.; Sayo, N.; Saito, T.; Taketomi, T.; Kumobayashi, H. J. Am. Chem. Soc. 1989, 111, 9134.  doi: 10.1021/ja00207a038

    99. [99]

      Miyashita, A.; Takaya, H.; Souchi, T.; Noyori, R. Tetrahedron 1984, 40, 1245.  doi: 10.1016/S0040-4020(01)82411-X

    100. [100]

      Wiles, J. A.; Bergens, S. H. Organometallics 1998, 17, 2228.  doi: 10.1021/om980113f

    101. [101]

      Wiles, J. A.; Bergens, S. H.; Young, V. G. Can. J. Chem. 2001, 79, 1019.  doi: 10.1139/v01-051

    102. [102]

      Wiles, J. A.; Daley, C. J. A.; Hamilton, R. J.; Leong, C. G.; Ber-gens, S. H. Organometallics 2004, 23, 4564.  doi: 10.1021/om049740x

    103. [103]

      Daley, C. J. A.; Wiles, J. A.; Bergens, S. H. Can. J. Chem. 1998, 76, 1447.  doi: 10.1139/v98-189

    104. [104]

      Daley, C. J. A.; Bergens, S. H. J. Am. Chem. Soc. 2002, 124, 3680.  doi: 10.1021/ja0102991

    105. [105]

      Daley, C. J. A.; Wiles, J. A.; Bergens, S. H. Inorg. Chim. Acta 2006, 359, 2760  doi: 10.1016/j.ica.2005.10.026

    106. [106]

      Kurono, N.; Uemura, M.; Ohkuma, T. Eur. J. Org. Chem. 2010, 1455.

    107. [107]

      Kurono, N.; Nii, N.; Sakaguchi, Y.; Uemura, M.; Ohkuma, T. Angew. Chem., Int. Ed. 2011, 50, 5541.  doi: 10.1002/anie.201100939

    108. [108]

      Uemura, M.; Kurono, N.; Sakai, Y.; Ohkuma, T. Adv. Synth. Catal. 2012, 354, 2023.  doi: 10.1002/adsc.v354.10

    109. [109]

      Zhao, X. X.; Ivanova, N.; Hadzovic, A.; Iuliis, M. Z. D.; Lough, A. J.; Morris, R. H. Organometallics 2008, 27, 503.  doi: 10.1021/om700360r

    110. [110]

      Ohta, T.; Tonomura, Y.; Nozaki, K.; Takaya, H.; Mashima, K. Organometallics 1996, 15, 1521.  doi: 10.1021/om9508905

    111. [111]

      Matteoli, U.; Beghetto, V.; Scrivanti, A. J. Mol. Catal. A:Chem. 1996, 109, 45.  doi: 10.1016/1381-1169(96)00039-8

    112. [112]

      Nispen, S. F. G. M.; Buijtenen, J.; Vekemans, J. A. J. M.; Meuldijkb, J.; Hulshof, L. A. Tetrahedron:Asymmetry 2006, 17, 2299.  doi: 10.1016/j.tetasy.2006.08.003

    113. [113]

      Taber, D. F.; Deker, P. B.; Silverberg, L. J. J. Org. Chem. 1992, 57, 5990.  doi: 10.1021/jo00048a037

    114. [114]

      Xie, B. H.; Lu, S. J.; Gao, L. Y.; Fu, H. X. J. Mol. Catal.(China) 1997, 11, 433(in Chinese).

    115. [115]

      Guerreiro, P.; Andrane, M. C. C.; Henry, J. C.; Tranchier, J. P.; Phansavath, P.; Ratovelomanana-Vidal, V.; Genet, J. P.; Homri, T.; Touati, A. R.; Hassine, B. B. Org. Organomet. Synth. 1999, 175.

    116. [116]

      Birdsall, D. J.; Hope, E. G.; Stuart, A. M.; Chen, W. P.; Hu, Y. L.; Xiao, J. L. Tetrahedron Lett. 2001, 42, 8551.  doi: 10.1016/S0040-4039(01)01835-4

    117. [117]

      Berthod, M.; Mignani, G.; Lemaire, M. Tetrahedron:Asymmetry 2004, 15, 1121.  doi: 10.1016/j.tetasy.2004.02.004

    118. [118]

      Geldbach, T. J.; Pregosin, P, S. Helv. Chim. Acta 2002, 85, 3937.  doi: 10.1002/1522-2675(200211)85:11<3937::AID-HLCA3937>3.0.CO;2-X

    119. [119]

      Thakur, V. V.; Nikalje, M. D.; Sudalai, A. Tetrahedron:Asym-metry 2003, 14, 581.  doi: 10.1016/S0957-4166(03)00024-7

    120. [120]

      Hu, Y. L.; Birdsall, D. J.; Stuart, A. M.; Hope, E. G.; Xiao, J. L. J. Mol. Catal. A:Chem. 2004, 219, 57.  doi: 10.1016/j.molcata.2004.05.009

    121. [121]

      Starodubtseva, E. V.; Turova, O. V.; Vinogradov, M. G.; Gorshkova, L. S.; Ferapontov, V. A.; Struchkova, M. I. Tetrahedron 2008, 64, 11713.  doi: 10.1016/j.tet.2008.10.012

    122. [122]

      Kockritz, A.; Bischoff, S.; Kant, M.; Siefken, R. J. Mol. Catal. A:Chem. 2001, 174, 119.  doi: 10.1016/S1381-1169(01)00193-5

    123. [123]

      Seki, T.; McEleney, K.; Crudden, C. M. Chem. Commun. 2012, 48, 6369.  doi: 10.1039/c2cc31247f

    124. [124]

      Xu, J. Y.; Ou, Z. M.; Yang, G. S. Zhejiang Chem. Ind. 2010, 41, 20(in Chinese).

    125. [125]

      Horn, J.; Bannwarth, W. Eur. J. Org. Chem. 2007, 2058.

    126. [126]

      Keshavarz, E.; Tabatabaeian, K.; Mamaghani, M.; Mahmoodi, N. O. Curr. Chem. Lett. 2012, 1, 91.  doi: 10.5267/j.ccl

    127. [127]

      Fan, Q. H.; Chen, Y. M.; Chen, X. M.; Jiang, D. Z.; Xi, F.; Chan, A. S. C. Chem. Commun. 2000, 789.

    128. [128]

      Deng, G. J.; Fan, Q. H.; Chen, X. M.; Liu, D, S.; Chan, A. S. C. Chem. Commun. 2002, 1570.

    129. [129]

      Deng, G. J.; Yi, B.; Huang, Y. Y.; Tang, W. J.; He, Y. M.; Fan, Q. H. Adv. Synth. Catal. 2004, 346, 1440.  doi: 10.1002/(ISSN)1615-4169

    130. [130]

      Huang, Y. Y.; He, Y. M.; Zhou, H. F.; Wu, L.; Li, B. L.; Fan, Q. H. J. Org. Chem. 2006, 71, 2874.  doi: 10.1021/jo052092m

    131. [131]

      Ma, B. D.; Deng, G. J.; Liu, J.; He, Y. M.; Fan, Q. H. Acta Chim. Sinica 2013, 71, 528(in Chinese).  doi: 10.6023/A13010156

    132. [132]

      Huang, Y. Y.; Yang, X.; Feng, Y.; Verpoort, F.; Fan, Q. F. J. Mol. Catal. A:Chem. 2014, 393, 150.  doi: 10.1016/j.molcata.2014.06.013

    133. [133]

      Liu, J.; Ma, B. D.; Feng, Y.; He, Y. M.; Fan, Q. H. Inorg. Chim. Acta 2014, 409, 106.  doi: 10.1016/j.ica.2013.05.035

    134. [134]

      Schinkel, M.; Wang, L. H.; Bielefeld, K.; Ackermann, L. Org. Lett. 2014, 16, 1876.  doi: 10.1021/ol500300w

    135. [135]

      Wang, X.; Lu, S. M.; Li, J.; Liu, Y.; Li, C. Catal. Sci. Technol. 2015, 5, 2585.  doi: 10.1039/C5CY00038F

    136. [136]

      Zhao, B. G.; Han, Z. B.; Ding, K. L. Angew. Chem., Int. Ed. 2013, 52, 4744.  doi: 10.1002/anie.v52.18

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