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Citation: Zheng-Le Zhao, Qing Gu, Xin-Yan Wu, Shu-Li You. Pd(0)-catalyzed benzylation of indole through η3-benzyl palladium intermediate[J]. Chinese Journal of Catalysis, ;2015, 36(1): 15-18. doi: 10.1016/S1872-2067(14)60191-1 shu

Pd(0)-catalyzed benzylation of indole through η3-benzyl palladium intermediate

  • 1.

    a Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Shanghai 200237, China;

  • Corresponding author: Shu-Li You, 
  • Received Date: 13 June 2014
    Available Online: 3 July 2014

    Fund Project: 国家重点基础研究发展计划(973计划, 2010CB833300) (973计划, 2010CB833300) 国家自然科学基金(21025209, 21121062, 21272253, 21332009). (21025209, 21121062, 21272253, 21332009)

  • An efficient method has been developed for the Pd(0)-catalyzed benzylation of indoles, which occurred with exclusive regioselectivity. When this reaction was performed in the presence of Pd(PPh3)4, it provided access to a broad range of substituted indoles bearing diarylmethanes at their 3-position in 90%-99% yields under mild conditions.
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    1. [1]

      [1] Tsuji J. Palladium Reagents and Catalysts. Chichester: John Wiley & Sons, 2004. 431

    2. [2]

      [2] Zhang X, Feng X J, Liu H S, Qin Y H, Dai Y. Chin J Catal (张新, 冯秀娟, 刘鹤松, 秦余虎, 戴耀. 催化学报), 2012, 33: 523

    3. [3]

      [3] Kuwano R, Kondo Y, Matsuyama Y. J Am Chem Soc, 2003, 125: 12104

    4. [4]

      [4] Kuwano R, Kondo Y. Org Lett, 2004, 6: 3545

    5. [5]

      [5] Ueno S, Komiya S, Tanaka T, Kuwano R. Org Lett, 2012, 14: 338

    6. [6]

      [6] Trost B M, Czabaniuk L C. J Am Chem Soc, 2010, 132: 15534

    7. [7]

      [7] Mukai T, Hirano K, Satoh T, Miura M. Org Lett, 2010, 12: 1360

    8. [8]

      [8] Legros J Y, Toffano M, Fiaud J C. Tetrahedron: Asymmetry, 1995, 6: 1899

    9. [9]

      [9] Trost B M, Czabaniuk L C. J Am Chem Soc, 2012, 134: 5778

    10. [10]

      [10] Trost B M, Czabaniuk L C. Chem Eur J, 2013, 19: 15210

    11. [11]

      [11] Legros J Y, Primault G, Toffano M, Rivière M A, Fiaud J C. Org Lett, 2000, 2: 433

    12. [12]

      [12] Yokogi M, Kuwano R. Tetrahedron Lett, 2007, 48: 6109

    13. [13]

      [13] Assié M, Meddour A, Fiaud J C, Legros J Y. Tetrahedron: Asymmetry, 2010, 21: 1701

    14. [14]

      [14] Fields W H, Chruma J J. Org Lett, 2010, 12: 316

    15. [15]

      [15] Torregrosa R R P, Ariyarathna Y, Chattopadhyay K, Tunge J A. J Am Chem Soc, 2010, 132: 9280

    16. [16]

      [16] Blessley G, Holden P, Walker M, Brown J M, Gouverneur V. Org Lett, 2012, 14: 2754

    17. [17]

      [17] Bao M, Nakamura H, Yamamoto Y. J Am Chem Soc, 2001, 123: 759

    18. [18]

      [18] Ariafard A, Lin Z Y. J Am Chem Soc, 2006, 128: 13010

    19. [19]

      [19] Lu S R, Xu Z W, Bao M, Yamamoto Y. Angew Chem Int Ed, 2008, 47: 4366

    20. [20]

      [20] Peng B, Feng X J, Zhang X, Ji L Y, Bao M. Tetrahedron, 2010, 66: 6013

    21. [21]

      [21] Peng B, Feng X J, Zhang X, Zhang S, Bao M. J Org Chem, 2010, 75: 2619

    22. [22]

      [22] Peng B, Zhang S, Yu X Q, Feng X J, Bao M. Org Lett, 2011, 13: 5402

    23. [23]

      [23] Feng X J, Sun A L, Zhang S, Yu X Q, Bao M. Org Lett, 2013, 15: 108

    24. [24]

      [24] Zhang X, Feng X J, Yu X Q, He R, Bao M. Org Biomol Chem, 2013, 11: 4016

    25. [25]

      [25] Feng X J, Song J L, Liu H S, Wang L G, Yu X Q, Bao M. RSC Adv, 2013, 3: 18985

    26. [26]

      [26] Zhang S, Wang Y, Feng X J, Bao M. J Am Chem Soc, 2012, 134: 5492

    27. [27]

      [27] Zhang S, Bao M. Synlett, 2012, 23: 2431

    28. [28]

      [28] Kuwano R, Kusano H. Org Lett, 2008, 10: 1979

    29. [29]

      [29] Kuwano R, KondoY, Shirahama T. Org Lett, 2005, 7: 2973

    30. [30]

      [30] Johns A M, Tye J W, Hartwig J F. J Am Chem Soc, 2006, 128: 16010

    31. [31]

      [31] Kuwano R. Synthesis, 2009: 1049

    32. [32]

      [32] Zhu Y, Rawal V H. J Am Chem Soc, 2012, 134: 111

    33. [33]

      [33] Lakhdar S, Westermaier M, Terrier F, Goumont R, Boubaker T, Ofial A R, Mayr H. J Org Chem, 2006, 71: 9088

    34. [34]

      [34] Skurydina D F, Tolkachev V N, Zenkina D I, Nikolaeva T G, Tolkachev O N. Pharm Chem J, 2008, 42: 443

    35. [35]

      [35] Duxbury D F. Chem Rev, 1993, 93: 381

    36. [36]

      [36] Shchepinov M S, Korshun V A. Chem Soc Rev, 2003, 32: 170

    37. [37]

      [37] Nair V, Thomas S, Mathew S C, Abhilash K G. Tetrahedron, 2006, 62: 6731

    38. [38]

      [38] He Q L, Sun F L, Zheng X J, You S L. Synlett, 2009: 1111

    39. [39]

      [39] Sun F L, Zheng X J, Gu Q, He Q L, You S L. Eur J Org Chem, 2010: 47

    40. [40]

      [40] Wu K, Jiang Y J, Fan Y S, Sha D, Zhang S Q. Chem Eur J, 2013, 19: 474

    41. [41]

      [41] Pape A R, Kaliappan K P, Kündig E P. Chem Rev, 2000, 100: 2917

    42. [42]

      [42] Roche S P, Porco J A Jr. Angew Chem Int Ed, 2011, 50: 4068

    43. [43]

      [43] Zhuo C X, Zhang W, You S L. Angew Chem Int Ed, 2012, 51: 12662

    44. [44]

      [44] Zhuo C X, Zheng C, You S L. Acc Chem Res, 2014, 47: 2558

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