Skip to main content
SpringerLink
Log in

Enantioselective catalysis of Suzuki reaction with planar-chiral CN-palladacycles: competition of two catalytic cycles

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The investigations of the catalysis of atroposelective Suzuki reaction with chiral CN-palladacycles showed that two competing catalytic cycles operate in this process, the relative contributions of each of them depend on the structure of the catalyst and reaction conditions. The reactions in aprotic medium at reduced temperature predominantly follow the pathway, in which the structure of palladacycle was retained, thus providing enantioselectivity up to 53% ee, when a nonmetallocene planar-chiral iminate CN-dimer was used as the catalyst. The structure of the μ-iodide cyclopalladated CN-dimer recovered upon reaction completion was confirmed by X-ray diffraction and spectroscopic studies of its triphenylphosphine derivative.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. L. N. Lewis, J. Am. Chem. Soc., 1986, 108, 743–749.

    Article  CAS  Google Scholar 

  2. W. A. Herrmann, C. Brossmer, K. Öfele, C.-P. Reisinger, T. Priermeier, M. Beller, H. Fischer, Angew. Chem., Int. Ed., 1995, 34, 1844–1848

    Article  CAS  Google Scholar 

  3. M. Beller, H. Fischer, W. A. Herrmann, K. Öfele, C. Brossmer, Angew. Chem., Int. Ed., 1995, 34, 1848–1849.

    Article  CAS  Google Scholar 

  4. M. Asay, D. Morales-Morales, Dalton Trans., 2015, 44, 17432–17447

    Article  CAS  Google Scholar 

  5. N. Selander, K. J. Szabó, Chem. Rev., 2011, 111, 2048–2076

    Article  CAS  Google Scholar 

  6. J. Dupont, C. S. Consorti, J. Spencer, Chem. Rev., 2005, 105, 2527–2571

    Article  CAS  Google Scholar 

  7. I. P. Beletskaya, A. V. Cheprakov, J. Organomet. Chem., 2004, 689, 4055–4082

    Article  CAS  Google Scholar 

  8. J. T. Singleton, Tetrahedron, 2003, 59, 1837–1857

    Article  CAS  Google Scholar 

  9. M. E. van der Boom, D. Milstein, Chem. Rev., 2003, 103, 1759–1792

    Article  CAS  Google Scholar 

  10. J. Dupont, M. Pfeffer, J. Spencer, Eur. J. Inorg. Chem., 2001, 1917–1927

    Google Scholar 

  11. M. Albrecht, G. van Koten, Angew. Chem., Int. Ed., 2001, 40, 3750–3781

    Article  CAS  Google Scholar 

  12. N. S. Khrushcheva, L. A. Bulygina, V. I. Sokolov, Russ. Chem. Bull. (Int. Ed.), 2012, 61, 1553–1555 [Izv. Akad. Nauk, Ser. Khim., 2012, 1537–1539].

    Article  CAS  Google Scholar 

  13. R. B. Bedford, in Palladacycles. Synthesis, Characterization and Applications, Eds J. Dupont, M. Pfeffer, Wiley-VCH, Weinheim, 2008, Ch. 9, 209–225

    Google Scholar 

  14. C. Nájera, D. A. Alonso, in Palladacycles. Synthesis, Characterization and Applications, Eds J. Dupont, M. Pfeffer, Wiley-VCH, Weinheim, 2008, Ch. 8, 155–207

    Google Scholar 

  15. N. Marion, S. P. Nolan, Acc. Chem. Res., 2008, 41, 1440–1449

    Article  CAS  Google Scholar 

  16. F. Bellina, A. Carpita, R. Rossi, Synthesis, 2004, 2419–2440

    Google Scholar 

  17. R. B. Bedford, C. S. J. Cazin, D. Holder, Coord. Chem. Rev., 2004, 248, 2283–2321

    Article  CAS  Google Scholar 

  18. R. B. Bedford, Chem. Commun., 2003, 1787–1796

    Google Scholar 

  19. N. J. Whitcombe, K. K. Hii, S. E. Gibson, Tetrahedron, 2001, 57, 7449–7476

    Article  CAS  Google Scholar 

  20. W. A. Herrmann, V. P. W. Böhm, C.-P. Reisinger, J. Organomet. Chem., 1999, 576, 23–41.

    Article  CAS  Google Scholar 

  21. P. Gautam, B.M. Bhanage, J. Org. Chem., 2015, 80, 7810–7815

    Article  CAS  Google Scholar 

  22. R. B. Bedford, C. S. J. Cazin, S. J. Coles, T. Gelbrich, M. B. Hursthouse, V. J. M. Scordia, J. Chem. Soc., Dalton Trans., 2003, 3350–3356

    Google Scholar 

  23. I. P. Beletskaya, A. N. Kashin, N. B. Karlstedt, A. V. Mitin, A. V. Cheprakov, G. M. Kazankov, J. Organomet. Chem., 2001, 622, 89–96

    Article  CAS  Google Scholar 

  24. J. M. Brunel, A. Heumann, G. Buono, Angew. Chem., Int. Ed., 2000, 39, 1946–1949

    Article  CAS  Google Scholar 

  25. A. S. Gruber, D. Zim, G. Ebeling, A. L. Monteiro, J. Dupont, Org. Lett., 2000, 2, 1287–1290

    Article  CAS  Google Scholar 

  26. M. Ohff, A. Ohff, D. Milstein, J. Chem. Soc., Chem. Commun., 1999, 357–358

    Google Scholar 

  27. F. Miyazaki, K. Yamaguchi, M. Shibasaki, Tetrahedron Lett., 1999, 40, 7379–7383

    Article  CAS  Google Scholar 

  28. D. A. Albisson, R. B. Bedford, P. N. Scully, Tetrahedron Lett., 1998, 39, 9793–9796

    Article  CAS  Google Scholar 

  29. W. A. Herrmann, C. Brossmer, C.-P. Reisinger, T. H. Riermeier, K. Ofele, M. Beller, Chem. Eur. J., 1997, 3, 1357–1364.

    Article  CAS  Google Scholar 

  30. R. Mamidala, V. Mukundam, K. Dhanunjayarao, K. Venkatasubbaiah, Dalton Trans., 2015, 44, 5805–5809

    Article  CAS  Google Scholar 

  31. E. Cook, K. Iwasaki, J. D. Masuda, A. Xia, Polyhedron, 2015, 87, 38–42

    Article  CAS  Google Scholar 

  32. L. Li, S. Zhao, A. Joshi-Pangu, M. Diane, M. R. Biscoe, J. Am. Chem. Soc., 2014, 136, 14027–14030

    Article  CAS  Google Scholar 

  33. M. Micksch, M. Tenne, T. Strassner, Organometallics, 2014, 33, 3966–3976

    Article  CAS  Google Scholar 

  34. A. Shen, C. Ni, Y.-C. Cao, H. Zhou, G.-H. Song, X.-F. Ye, Tetrahedron Lett., 2014, 55, 3278–3282

    Article  CAS  Google Scholar 

  35. W. Susanto, C.-Y. Chu, W. J. Ang, T.-C. Chou, L.-C. Lo, Y. Lam, J. Org. Chem., 2012, 77, 2729–2742

    Article  CAS  Google Scholar 

  36. Y.-J. Kim, J.-H. Lee, T. Kim, J. Ham, Z. N. Zheng, S. W. Lee, Eur. J. Inorg. Chem., 2012, 6011–6017.

    Google Scholar 

  37. C. Xu, H.-M. Li, Z.-Q. Xiao, Z.-Q. Wang, S.-F. Tang, B.-M. Ji, X.-Q. Hao, M.-P. Song, Dalton Trans., 2014, 43, 10235–10247

    Article  CAS  Google Scholar 

  38. O. Navarro, N. Marion, Y. Oonishi, R. A. Kelly III, S. P. Nolan, J. Org. Chem., 2006, 71, 685–692

    Article  CAS  Google Scholar 

  39. O. Navarro, R. A. Kelly, S. P. Nolan, J. Am. Chem. Soc., 2003, 125, 16194–16195

    Article  CAS  Google Scholar 

  40. D. Zim, A. S. Gruber, G. Ebeling, J. Dupont, A. L. Monteiro, Org. Lett., 2000, 2, 2881–2884.

    Article  CAS  Google Scholar 

  41. D.-L. Mo, T.-K. Zhang, G.-C. Ge, X.-J. Huang, C.-H. Ding, L.-X. Dai, X.-L. Hou, Synlett, 2014, 25, 2686–2702

    Article  CAS  Google Scholar 

  42. V. V. Dunina, O. N. Gorunova, P. A. Zykov, K. A. Kochetkov, Russ. Chem. Rev., 2011, 80, 51–74

    Article  CAS  Google Scholar 

  43. Y. Canac, R. Chauvin, Eur. J. Inorg. Chem., 2010, 2325–2335

    Google Scholar 

  44. J. Spencer, in Palladacycles. Synthesis, Characterization and Applications, Eds J. Dupont, M. Pfeffer, Wiley-VCH, Weinheim, 2008, Ch. 10, 227–238.

    Google Scholar 

  45. T. Hellmuth, S. Rieckhoff, M. Weiss, K. Dorst, W. Frey, R. Peters, ACS Catal., 2014, 4, 1850–1858

    Article  CAS  Google Scholar 

  46. H. Nomura, C. J. Richards, Chem. Asian J., 2010, 5, 1726–1740

    Article  CAS  Google Scholar 

  47. S. H. Eitel, M. Bauer, D. Schweinfurth, N. Deibel, B. Sarkar, H. Kelm, H.-J. Krüger, W. Frey, R. Peters, J. Am. Chem. Soc., 2012, 134, 4683–4693

    Article  CAS  Google Scholar 

  48. M. Weiss, W. Frey, R. Peters, Organometallics, 2012, 31, 6365–6372

    Article  CAS  Google Scholar 

  49. J. S. Cannon, A. C. Olson, L. E. Overman, N. S. Solomon, J. Org. Chem., 2012, 77, 1961–1973

    Article  CAS  Google Scholar 

  50. J. S. Cannon, S. F. Kirsch, L. E. Overman, J. Am. Chem. Soc., 2010, 132, 15185–15191.

    Article  CAS  Google Scholar 

  51. R. J. Chew, P.-H. Leung, Chem. Rec., 2016, 16, 141–158

    Article  CAS  Google Scholar 

  52. X.-Y. Yang, W.S. Tay, Y. Li, S. A. Pullarkat, P.-H. Leung, Organometallics, 2015, 34, 1582–1588

    Article  CAS  Google Scholar 

  53. K. Gan, A. Sadeer, C. Xu, Y. Li, S. A. Pullarkat, Organometallics, 2014, 33, 5074–5076

    Article  CAS  Google Scholar 

  54. X.-Y. Yang, J. H. Gan, Y. Li, S. A. Pullarkat, P.-H. Leung, Dalton Trans., 2015, 44, 1258–1263

    Article  CAS  Google Scholar 

  55. J. Lu, J. Ye, W.-L. Duan, Org. Lett., 2013, 15, 5016–5019

    Article  CAS  Google Scholar 

  56. Y. Huang, R. J. Chew, S. A. Pullarkat, Y. Li, P.-H. Leung, J. Org. Chem., 2012, 77, 6849–6854.

    Article  CAS  Google Scholar 

  57. C. Schrapel, R. Peters, Angew. Chem., Int. Ed., 2015, 54, 10289–10293

    Article  CAS  Google Scholar 

  58. K. Hyodo, S. Nakamura, N. Shibata, Angew. Chem., Int. Ed., 2012, 51, 10337–10341

    Article  CAS  Google Scholar 

  59. M. Weber, S. Jautze, W. Frey, R. Peters, Chem. Eur. J., 2012, 18, 14792–14804

    Article  CAS  Google Scholar 

  60. M. Weber, R. Peters, J. Org. Chem., 2012, 77, 10846–10855

    Article  CAS  Google Scholar 

  61. M. Weber, S. Jautze, W. Frey, R. Peters, J. Am. Chem. Soc., 2010, 132, 12222–12225.

    Article  CAS  Google Scholar 

  62. F. K. Friedlein, K. Kromm, F. Hampel, J. A. Gladysz, Chem. Eur. J., 2006, 12, 5267–5281

    Article  CAS  Google Scholar 

  63. M. Rosol, A. Moyano, J. Organomet. Chem., 2005, 690, 2291–2296

    Article  CAS  Google Scholar 

  64. K. Yuan, T. K. Zhang, X. L. Hou, J. Org. Chem., 2005, 70, 6085–6088

    Article  CAS  Google Scholar 

  65. D. Morales-Morales, R. E. Cramer, C. M. Jensen, J. Organomet. Chem., 2002, 654, 44–50

    Article  CAS  Google Scholar 

  66. J. Bravo, C. Cativiela, R. Navarro, E. P. Urriolabeitia, J. Organomet. Chem., 2002, 650, 157–172

    Article  CAS  Google Scholar 

  67. J. Dupont, A. S. Gruber, G. S. Fonsec, A. L. Monteiro, G. Ebeling, Organometallics, 2001, 20, 171–176.

    Article  CAS  Google Scholar 

  68. I. P. Beletskaya, A. V. Cheprakov, in New Trends in Cross-Coupling: Theory and Applications., Ed. T. J. Colacot, RSC Catalysis Series, 2014, Vol. 21, Ch. 9, pp. 355–478

    Book  Google Scholar 

  69. I. P. Beletskaya, A. V. Cheprakov, Chem. Rev., 2000, 100, 3009–3066.

    Article  CAS  Google Scholar 

  70. H. Zhang, A. Lei, Dalton Trans., 2011, 40, 8745–8754

    Article  CAS  Google Scholar 

  71. R. Gerber, O. Blacque, C. M. Frech, ChemCatChem, 2009, 1, 393–400

    Article  CAS  Google Scholar 

  72. D. Morales-Morales, R. Redón, C. Yung, C. M. Jensen, Chem. Commun., 2000, 1619–1620

    Google Scholar 

  73. D. Morales-Morales, C. Grause, K. Kasaoka, R. Redón, R. E. Cramer, C. M. Jensen, Inorg. Chim. Acta, 2000, 300–302, 958–963

    Article  Google Scholar 

  74. H. Weissman, D. Milstein, J. Chem. Soc., Chem. Commun., 1999, 1901–1902

    Google Scholar 

  75. M. Ohff, A. Ohff, M. E. van der Boom, D. Milstein, J. Am. Chem. Soc., 1997, 119, 11687–1688.

    Article  CAS  Google Scholar 

  76. F. N. Hosseini, A. Ariafard, M. Rashidi, G. Azimi, S. M. Nabavizadeh, J. Organomet. Chem., 2011, 696, 3351–3358

    Article  CAS  Google Scholar 

  77. R. Gerber, O. Blacque, C. M. Frech, Dalton Trans., 2011, 40, 8996–9003

    Article  CAS  Google Scholar 

  78. L. Xue, Z. Lin, Chem. Soc. Rev., 2010, 39, 1692–1705

    Article  CAS  Google Scholar 

  79. O. Blacque, C. M. Frech, Chem. Eur. J., 2010, 16, 1521–1531

    Article  CAS  Google Scholar 

  80. J. L. Bolliger, O. Blacque, C. M. Frech, Chem. Eur. J., 2008, 14, 7969–7977

    Article  CAS  Google Scholar 

  81. A. Sundermann, O. Uzan, J. M. L. Martin, Chem. Eur. J., 2001, 7, 1703–1711.

    Article  CAS  Google Scholar 

  82. S. Ramírez-Rave, F. Estudiante-Negrete, R. A. Toscano, S. Hernández-Ortega, D. Morales-Morales, J.-M. Grévy, J. Organomet. Chem., 2014, 749, 287–295

    Article  CAS  Google Scholar 

  83. A. Avila-Sorrosa, F. Estudiante-Negrete, S. Hernández-Ortega, R. A. Toscano, D. Morales-Morales, Inorg. Chim. Acta, 2010, 363, 1262–1268

    Article  CAS  Google Scholar 

  84. D. Olsson, O. F. Wendt, J. Organomet. Chem., 2009, 694, 3112–3115

    Article  CAS  Google Scholar 

  85. J. L. Bolliger, O. Blacque, C. M. Frech, Angew. Chem., Int. Ed., 2007, 46, 6514–6517.

    Article  CAS  Google Scholar 

  86. T. Takemoto, S. Iwasa, H. Hamada, K. Shibatomi, M. Kameyama, Y. Motoyamac, H. Nishiyama, Tetrahedron Lett., 2007, 48, 3397–3401.

    Article  CAS  Google Scholar 

  87. S. Sjövall, O. F. Wendt, C. Andersson, J. Chem. Soc., Dalton Trans., 2002, 1396–1400

    Google Scholar 

  88. W. A. Herrmann, C. P. Reisinger, K. Öfele, C. Brossmer, M. Beller, H. Fischer, J. Mol. Catal. A: Chem., 1996, 108, 51–56.

    Article  CAS  Google Scholar 

  89. A. Tenaglia, L. Giordano, G. Buono, Org. Lett., 2006, 8, 4315–4318.

    Article  CAS  Google Scholar 

  90. I. Vicente-Hernández, M.-T. Chicote, J. Vicente, D. Bautista, Chem. Commun., 2016, 52, 594–596

    Article  CAS  Google Scholar 

  91. F. Juliá-Hernández, A. Arcas, J. Vicente, Chem. Eur. J., 2012, 18, 7780–7786

    Article  CAS  Google Scholar 

  92. J. Vicente, A. Arcas, F. Juliá-Hernández, D. Bautista, Angew. Chem., Int. Ed., 2011, 50, 6896–6899.

    Article  CAS  Google Scholar 

  93. N. T. S. Phan, M. van der Sluys, C. W. Jones, Adv. Synth. Catal., 2006, 348, 609–679

    Article  CAS  Google Scholar 

  94. P. Espinet, A. M. Echavarren, Angew. Chem., Int. Ed., 2004, 43, 4704–4734

    CAS  Google Scholar 

  95. M. R. Eberhard, Org. Lett., 2004, 6, 2125–2128.

    Article  CAS  Google Scholar 

  96. M. García-Melchor, A. A. C. Braga, A. Lledós, G. Ujaque, F. Maseras, Acc. Chem. Res., 2013, 46, 2626–2634

    Article  CAS  Google Scholar 

  97. A. A. C. Braga, G. Ujaque, F. Maseras, Organometallics, 2006, 25, 3647–3658.

    Article  CAS  Google Scholar 

  98. W. A. Herrmann, K. Öfele, D. v. Preysing, S. K. Schneider, J. Organomet. Chem., 2003, 687, 229–248.

    Article  CAS  Google Scholar 

  99. F. Proutiere, F. Schoenebeck, Synlett, 2012, 645–648

    Google Scholar 

  100. F. Proutiere, F. Schoenebeck, Angew. Chem., Int. Ed., 2011, 50, 8192–8195

    Article  CAS  Google Scholar 

  101. L. J. Goossen, D. Koley, H. L. Hermann, W. Thiel, Organometallics, 2006, 25, 54–67

    Article  CAS  Google Scholar 

  102. L. J. Goossen, D. Koley, H. L. Hermann, W. Thiel, J. Am. Chem. Soc., 2005, 127, 11102–11114

    Article  CAS  Google Scholar 

  103. S. Kozuch, S. Shaik, A. Jutand, C. Amatore, Chem. Eur. J., 2004, 10, 3072–3080

    Article  CAS  Google Scholar 

  104. C. Amatore, A. Jutand, F. Lemaître, J. L. Ricard, S. Kozuch, S. Shaik, J. Organomet. Chem., 2004, 689, 3728–3734

    Article  CAS  Google Scholar 

  105. C. Amatore, A. Jutand, Acc. Chem. Res., 2000, 33, 314–321.

    Article  CAS  Google Scholar 

  106. A. Suzuki, Angew. Chem., Int. Ed., 2011, 50, 6722–6737

    Article  CAS  Google Scholar 

  107. N. Miyaura, J. Organomet. Chem., 2002, 653, 54–57

    Article  CAS  Google Scholar 

  108. A. Suzuki, J. Organomet. Chem., 1999, 576, 147–168

    Article  CAS  Google Scholar 

  109. N. Miyaura, A. Suzuki, Chem. Rev., 1995, 95, 2457–2483.

    Article  CAS  Google Scholar 

  110. A. Bruneau, M. Roche, M. Alami, S. Messaoudi, ACS Catal., 2015, 5, 1386–1396

    Article  CAS  Google Scholar 

  111. A. Dewan, Z. Buragohain, M. Mondal, G. Sarmah, G. Borah, U. Bora, Appl. Organomet. Chem., 2014, 28, 230–233

    Article  CAS  Google Scholar 

  112. K. Karami, N. Rahimi, M. B. Shehni, Tetrahedron Lett., 2012, 53, 2428–2431

    Article  CAS  Google Scholar 

  113. T. Kinzel, Y. Zhang, S. L. Buchwald, J. Am. Chem. Soc., 2010, 132, 14073–14075

    Article  CAS  Google Scholar 

  114. B. Mu, T. Li, J. Li, Y. Wu, J. Organomet. Chem., 2008, 693, 1243–1251

    Article  CAS  Google Scholar 

  115. N. S. Khrushcheva, L. A. Bulygina, Z. A. Starikova, V. I. Sokolov, Russ. Chem. Bull. (Int. Ed.), 2014, 63, 883–889 [Izv. Akad. Nauk, Ser. Khim., 2014, 883–889]

    Article  CAS  Google Scholar 

  116. N. S. Khruscheva, L. A. Bulygina, V. I. Sokolov, Russ. Chem. Bull. (Int. Ed.), 2011, 60, 503–505 [Izv. Akad. Nauk, Ser. Khim., 2011, 493–495].

    Article  CAS  Google Scholar 

  117. G. Bringmann, T. Gulder, T. A. M. Gulder, M. Breuning, Chem. Rev., 2011, 111, 563–639

    Article  CAS  Google Scholar 

  118. J. Magano, J. R. Dunetz, Chem. Rev., 2011, 111, 2177–2250

    Article  CAS  Google Scholar 

  119. O. Baudoin, Eur. J. Org. Chem., 2005, 4223–4229

    Google Scholar 

  120. J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev., 2002, 102, 1359–1469

    Article  CAS  Google Scholar 

  121. K. Kamikawa, M. Uemura, Synlett, 2000, 938–949

    Google Scholar 

  122. G. Bringmann, M. Breuning, S. Tasler, Synthesis, 1999, 525–558

    Google Scholar 

  123. S. P. Stanforth, Tetrahedron, 1998, 54, 263–303

    Article  CAS  Google Scholar 

  124. L. A. Bulygina, N. S. Khrushcheva, S. M. Peregudova, V. I. Sokolov, Russ. Chem. Bull. (Int. Ed.), 2012, 61, 1998–2000 [Izv. Akad. Nauk, Ser. Khim., 2012, 1980–1982]

    Article  CAS  Google Scholar 

  125. V. I. Sokolov, L. A. Bulygina, N. S. Khrushcheva, N. S. Ikonnikov, Russ. Chem. Bull. (Int. Ed.), 2010, 59, 1400–1402 [Izv. Akad. Nauk, Ser. Khim., 2010, 1370–1372].

    Article  CAS  Google Scholar 

  126. D. Zhang, Q. Wang, Coord. Chem. Rev., 2015, 286, 1–16

    Article  CAS  Google Scholar 

  127. Y. Akai, L. Konnert, T. Yamamoto, M. Suginome, Chem. Commun., 2015, 51, 7211–7214

    Article  CAS  Google Scholar 

  128. G. Xu, W. Fu, G. Liu, C. H. Senanayake, W. Tang, J. Am. Chem. Soc., 2014, 136, 570–573

    Article  CAS  Google Scholar 

  129. G. Liu, G. Xu, R. Luo, W. Tang, Synlett, 2013, 24, 2465–2471

    Article  CAS  Google Scholar 

  130. Y. Zhou, S. Wang, W. Wu, Q. Li, Y. He, Y. Zhuang, L. Li, J. Pang, Z. Zhou, L. Qiu, Org. Lett., 2013, 15, 5508–5511

    Article  CAS  Google Scholar 

  131. S. Wang, J. Li, T. Miao, W. Wu, Q. Li, Y. Zhuang, Z. Zhou, L. Qiu, Org. Lett., 2012, 14, 1966–1969.

    Article  CAS  Google Scholar 

  132. J.-L. Niu, X.-Q. Hao, J.-F. Gong, M.-P. Song, Dalton Trans., 2011, 40, 5135–5150

    Article  CAS  Google Scholar 

  133. B.-S. Zhang, W. Wang, D.-D. Shao, X.-Q. Hao, J.-F. Gong, M.-P. Song, Organometallics, 2010, 29, 2579–2587.

    Article  CAS  Google Scholar 

  134. T. Wang, X.-Q. Hao, J.-J. Huang, K. Wang, J.-F. Gong, M.-P. Song, Organometallics, 2014, 33, 194–205.

    Article  CAS  Google Scholar 

  135. O. N. Gorunova, M. V. Livantsov, Yu. K. Grishin, M. M. Ilyin, Jr., K. A. Kochetkov, A. V. Churakov, L. G. Kuz´mina, V. N. Khrustalev, V. V. Dunina, J. Organomet. Chem., 2013, 737, 59–63.

    Article  CAS  Google Scholar 

  136. O. N. Gorunova, P. A. Zykov, M. V. Livantsov, K. A. Kochetkov, Yu. K. Grishin, V. V. Dunina, Russ. Chem. Bull. (Int. Ed.), 2010, 59, 1840–1842 [Izv. Akad. Nauk, Ser. Khim., 2010, 1791–1793].

    Article  CAS  Google Scholar 

  137. L. A. Bulygina, N. S. Khrushcheva, Ya. A. Gur´eva, A. V. Kutchin, V. I. Sokolov, Russ. Chem. Bull. (Int. Ed.), 2015, 64, 436–438 [Izv. Akad. Nauk, Ser. Khim., 2015, 436–438]

    Article  CAS  Google Scholar 

  138. L. A. Bulygina, N. S. Khrushcheva, A. S. Peregudov, V. I. Sokolov, Russ. Chem. Bull. (Int. Ed.), 2015, 64, 146–150 [Izv. Akad. Nauk, Ser. Khim., 2015, 146–150].

    Article  CAS  Google Scholar 

  139. M. E. Günay, C. J. Richards, Organometallics, 2009, 28, 5833–5836

    Article  CAS  Google Scholar 

  140. J. C. Gaunt, B. L. Shaw, J. Organomet. Chem., 1975, 102, 511–516.

    Article  CAS  Google Scholar 

  141. L. L. Troitskaya, L. A. Bulygina, V. I. Sokolov, Russ. Chem. Bull. (Int. Ed.), 1994, 43, 1253–1259 [Izv. Akad. Nauk, Ser. Khim., 1994, 1315–1321]

    Article  Google Scholar 

  142. N. A. Kataeva, Yu. K. Grishin, V. V. Dunina, Russ. Chem. Bull. (Int. Ed.), 2001, 50, 1323–1325 [Izv. Akad. Nauk, Ser. Khim., 2001, 1260–1262].

    Article  CAS  Google Scholar 

  143. V. V. Dunina, E. I. Turubanova, O. N. Gorunova, M. V. Livantsov, K. A. Lyssenko, D. Y. Antonov, Yu. K. Grishin, Polyhedron, 2012, 31, 413–421.

    Article  CAS  Google Scholar 

  144. V. V. Dunina, E. I. Turubanova, M. V. Livantsov, K. A. Lyssenko, N. V. Vorontsova, D. Yu. Antonov, Yu. K. Grishin, Tetrahedron: Asymmetry, 2009, 20, 1661–1671.

    Article  CAS  Google Scholar 

  145. D. G. Allen, G. M. McLaughlin, G. B. Robertson, W. L. Steffen, G. Salem, S. B. Wild, Inorg. Chem., 1982, 21, 1007–1014.

    Article  CAS  Google Scholar 

  146. A. Bermejo, A. Ros, R. Fernández, J. M. Lassaletta, J. Am. Chem. Soc., 2008, 130, 15798–15799

    Article  CAS  Google Scholar 

  147. J. M. Wilson, D. J. Cram, J. Org. Chem., 1984, 49, 4930–4943.

    Article  CAS  Google Scholar 

  148. A. R. Kapdi, G. Dhangar, J. L. Serrano, J. Pérez, L. García, I. J. S. Fairlamb, Chem. Commun., 2014, 50, 9859–9861

    Article  CAS  Google Scholar 

  149. J. L. Serrano, L. García, J. Pérez, E. Pérez, J. García, G. Sánchez, P. Sehnal, S. De Ornellas, T. J. Williams, I. J. S. Fairlamb, Organometallics, 2011, 30, 5095–5109

    Article  CAS  Google Scholar 

  150. D. Zim1, S. M. Nobre, A. L. Monteiro, J. Mol. Catal. A: Chem., 2008, 287, 16–23

    Article  CAS  Google Scholar 

  151. J. Louie, J. F. Hartwig, Angew. Chem., Int. Ed., 1996, 35, 2359–2361.

    Article  CAS  Google Scholar 

  152. C. Amatore, A. Jutand, G. Le Duc, Angew. Chem., Int. Ed., 2012, 51, 1379–1382.

    Article  CAS  Google Scholar 

  153. L. A. Bulygina, N. S. Khrushcheva, V. I. Sokolov, Russ. Chem. Bull. (Int. Ed.), 2011, 60, 258–260 [Izv. Akad. Nauk, Ser. Khim., 2011, 252–254].

    Article  CAS  Google Scholar 

  154. A. R. Hajipoura, F. Rafiee, Appl. Organomet. Chem., 2013, 27, 412–418

    Article  CAS  Google Scholar 

  155. C. Xu, J.-F. Gong, S.-F. Yue, Y. Zhu, Y.-J. Wu, Dalton Trans., 2006, 4730–4739.

    Google Scholar 

  156. J. T. Sharp, I. Gosney, A. G. Rowley, in Practical Organic Chemistry–A Student Handbook of Techniques, Chapman and Hall, London, 1989, Ch. 4.2.2d.

    Book  Google Scholar 

  157. A.-S. Castanet, F. Colobert, P.-E. Broutin, M. Obringer, Tetrahedron: Asymmetry, 2002, 13, 659–665.

    Article  CAS  Google Scholar 

  158. C. D. Braddock, S. C. Tucker, J. M. Brown, Bull. Soc. Chem. Fr., 1997, 134, 399–410.

    CAS  Google Scholar 

  159. V. Lucchini, P. R. Wells, Org. Magn. Res., 1976, 8, 137–140.

    Article  CAS  Google Scholar 

  160. G. M. Sheldrick, SADABS. Program for Scaling and Correction of Area Detector Data, University of Göttingen, Göttingen, Germany, 1997.

    Google Scholar 

  161. G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., 2008, 64, 112–122.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    O. N. Gorunova, M. M. Ilyin & K. A. Kochetkov

  2. Department of Chemistry, M. V. Lomonosov Moscow State University, Build. 3, 1 Leninskie Gory, 119991, Moscow, Russian Federation

    Yu. K. Grishin & V. V. Dunina

  3. N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, 31 Leninsky prosp., 119991, Moscow, Russian Federation

    A. V. Churakov & L. G. Kuz´mina

Authors
  1. O. N. Gorunova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yu. K. Grishin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. M. Ilyin
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. K. A. Kochetkov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. V. Churakov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. L. G. Kuz´mina
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. V. V. Dunina
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. V. Dunina.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 0282—0292, February, 2017.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Gorunova, O.N., Grishin, Y.K., Ilyin, M.M. et al. Enantioselective catalysis of Suzuki reaction with planar-chiral CN-palladacycles: competition of two catalytic cycles. Russ Chem Bull 66, 282–292 (2017). https://doi.org/10.1007/s11172-017-1729-4

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-017-1729-4

Key words

Search

Navigation