Citation: CHEN Sheng, HAN Jian-Lin*, LI Gui-Gen, PAN Yi*. K2CO3/Ni(OAc)2 Catalyzed Aminobromination of β-Methyl-β-nitrostyrenes with Benzamide/N, N-Dibromobenzamide as Nitrogen/Bromine Source[J]. Chinese Journal of Inorganic Chemistry, ;2014, 30(1): 213-219. doi: 10.11862/CJIC.2014.042 shu

K2CO3/Ni(OAc)2 Catalyzed Aminobromination of β-Methyl-β-nitrostyrenes with Benzamide/N, N-Dibromobenzamide as Nitrogen/Bromine Source

  • Received Date: 24 June 2013
    Available Online: 24 October 2013

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  • An efficient and facile aminobromination reaction of β-methyl-β-nitrostyrenes with PhCONH2/PhCONBr2 as nitrogen/bromine source has been developed, which could tolerate a wide scope of substrates with good chemical yield and diastereoselectivity. This aminobrominaiton system uses metal salt and base as the co-catalyst, which is different from our previous reported systems.
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    1. [1]

      [1] Kemp J E. Comprehensive Organic Synthesis: Vol.3; Trost B M, Fleming I, Eds.; Oxford: Pergamon Press, 1991:469-513

    2. [2]

      [2] Yeung Y Y, Gao X, Corey E J. J. Am. Chem. Soc., 2006, 128:9644-9645

    3. [3]

      [3] Griffith D A, Danishefsky S J. J. Am. Chem. Soc., 1991, 113: 5863-5864

    4. [4]

      [4] Lessard J, Driguez H, Vermes J P. Tetrahedron Lett., 1970, 11:4887-4891

    5. [5]

      [5] Daniher F A, Butler P E. J. Org. Chem., 1968, 33:4336-4340

    6. [6]

      [6] Orlek B S, Stemp G. Tetrahedron Lett., 1991, 32:4045-4048

    7. [7]

      [7] Manzoni M R, Zabawa T P, Kasi D, et al. Organometallics, 2004, 23:5618-5621

    8. [8]

      [8] Danielec H, Klugge J, Schlummer B, et al. Synthesis, 2006: 551-556

    9. [9]

      [9] Xu L, Du H F, Shi Y. J. Org. Chem., 2007, 72:7038-7041

    10. [10]

      [10] Du H F, Zhao B G, Shi Y. J. Am. Chem. Soc., 2007, 129: 762-763

    11. [11]

      [11] Li G, Saibabu Kotti S R S, Timmons C. Eur. J. Org. Chem., 2007:2745-2758

    12. [12]

      [12] Qui J, Silverman R B. J. Med. Chem., 2000, 43:706-720

    13. [13]

      [13] Chen D, Timmons C, Guo L, et al. Synthesis, 2004:2749-2784

    14. [14]

      [14] Chen D, Kim S H, Hodges B, et al. ARKIVOC, 2003(xii): 56-62

    15. [15]

      [15] Chen D, Guo L, Liu J, et al. Org. Lett., 2005, 7:921-924

    16. [16]

      [16] Mei H B, Yan L J, Han J L, et al. Chem. Biol. Drug Des., 2010, 76:392-396

    17. [17]

      [17] Zhang G Q, An G H, Zheng J, et al. Tetrahedron Lett., 2010, 51:987-989

    18. [18]

      [18] Li G, Wei H X, Kim S H, et al. Org. Lett., 1999, 1:395-397

    19. [19]

      [19] Wei H X, Kim S H, Li G. Tetrahedron, 2001, 57:3869-3871

    20. [20]

      [20] Han J L, Zhi S J, Wang L Y, et al. Eur. J. Org. Chem., 2007: 1332-1337

    21. [21]

      [21] Sun H, Zhang G Q, Zhi S J, et al. Org. Biol. Chem., 2010, 8: 4236-4239

    22. [22]

      [22] Chen Z G, Wei J F, Li R T, et al. J. Org. Chem., 2009, 74: 1371-1373

    23. [23]

      [23] Thakur V V, Talluri S K, Sudalai A. Org. Lett., 2003, 5:861-864

    24. [24]

      [24] Wu X L, Xia J J, Wang G W. Org. Biomol. Chem., 2008, 6: 548-553

    25. [25]

      [25] Wei J F, Zhang L H, Chen Z G, et al. Org. Biomol. Chem., 2009, 7:3280-3284

    26. [26]

      [26] Li W L, Chen Z G, Zhou J M, et al. Chin. J. Chem., 2012, 30:830-836

    27. [27]

      [27] Qi M H, Shao L X, Shi M. Chin. J. Chem., 2011, 29:2739-2743

    28. [28]

      [28] Zhi S J, Han J L, Lin C, et al. Synthesis, 2008:1570-1574

    29. [29]

      [29] Zhi S J, Sun H, Lin C, et al. Sci. China Chem., 2010, 53: 140-146

    30. [30]

      [30] Zhi S J, Mei H B, Zhang G Q, et al. Sci. China Chem., 2010, 53:1946-1952

    31. [31]

      [31] Qian Y, Ji X Y, Zhou W, et al. Tetrahedron, 2012, 68:6198-6203

    32. [32]

      [32] Mei H B, Han J L, Li G, et al. RSC Adv., 2011, 1:429-433

    33. [33]

      [33] Mei H B, Xiong Y W, Qian Y, et al. RSC Adv., 2012, 2:151-155

    34. [34]

      [34] Ji X Y, Mei H B, Qian Y, et al. Synthesis, 2011:3680-3686

    35. [35]

      [35] Ji X Y, Duan Z Q, Qian Y, et al. RSC Adv., 2012, 2:5565-5570

    36. [36]

      [36] Chen Z G, Zhao P F, Wang Y. Eur. J. Org. Chem., 2011: 5887-5893

    37. [37]

      [37] Chen Z G, Wang Y, Wei J F, et al. J. Org. Chem., 2010, 75: 2085-2088

    38. [38]

      [38] Zhi S J, Sun H, Zhang G Q, et al. Org. Biomol. Chem., 2010, 8:628-631

    39. [39]

      [39] Zhi S J, An G H, Sun H, et al. Tetrahedron Lett., 2010, 51: 2745-2747

    40. [40]

      [40] Enders D, Wiedemann J. Synthesis, 1996:1443-1450

    41. [41]

      [41] Lucet D, Toupet L, Gall T L, et al. J. Org. Chem., 1997, 62: 2682-2683

    42. [42]

      [42] Chen S, Han J L, Li G G, et al. Tetrahedron Lett., 2013, 54: 2781-2784

    43. [43]

      [43] Chudasama V, Wilden J D. Chem. Commun., 2008:3768-3770

    44. [44]

      [44] Ferjancic Z, Matovic R, Saicic R N. Tetrahedron, 2006, 62: 8503-8514

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