Citation: Li Dongjun, Wu Yanfang, Chang Honghong, Gao Wenchaoa, Wei Wenlong, Li Xing. Research Progress in the Cycloaddition Reactions of Nitroso Compounds[J]. Chinese Journal of Organic Chemistry, ;2016, 36(9): 1994-2010. doi: 10.6023/cjoc201604001 shu

Research Progress in the Cycloaddition Reactions of Nitroso Compounds

  • Corresponding author: Li Xing, lixing@tyut.edu.cn
  • Received Date: 1 April 2016
    Revised Date: 13 May 2016

    Fund Project: the Natural Science Foundation of Shanxi Province 2012021007-2

Figures(18)

  • The recent progress in the cycloaddition reactions of nitroso compounds with various compounds is reviewed, including[2+2], [3+2], [2+2+1], [3+3], [4+1] and [4+2] cycloaddition reactions. Moreover, the prospects of future development are also discussed.
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    1. [1]

      Wang, W.; Lu, X. H.; Dong, X. C.; Zhao, W. L. Chin. J. Org. Chem. 2015, 35, 137(in Chinese).
      (王雯, 陆秀宏, 董肖椿, 赵伟利, 有机化学, 2015, 35, 137.)
      (b) Wu, Y. Q.; Yu, L. Y.; Zhang, Q.; Li, L. D. Chin. J. Org. Chem. 2015, 35, 724(in Chinese).
      (吴玉芹, 于凉云, 张奇, 李立冬, 有机化学, 2015, 35, 724.)
      (c) Zheng, J. F.; Xie, Z. Q.; Chen, X. J.; Huang, P. Q. Acta Chim. Sinica 2015, 73, 705.
      (d) Cheng, G.; Yang, D. Q. Chin. J. Org. Chem. 2015, 35, 2023(in Chinese).
      (程果, 杨定乔, 有机化学, 2015, 35, 2023.)
      (e) Li, G. D.; Hu, H. Y.; Kan, Y. H.; Ma, K. R. Chin. J. Org. Chem. 2014, 34, 903(in Chinese).
      (李国栋, 胡华友, 阚玉和, 马奎蓉, 有机化学, 2014, 34, 903.)
      (f) Li, Q. H.; Huang, R.; Wang, C. J. Acta Chim. Sinica 2014, 72, 830(in Chinese).
      (李清华, 黄蓉, 王春江, 化学学报, 2014, 72, 830.)
      (g) Sun, L. H.; Liang, Z. Q.; Ye, S. Acta Chim. Sinica 2014, 72, 841(in Chinese).
      (孙利辉, 梁志钦, 叶松, 化学学报, 2014, 72, 841.)
      (h) Xie, M. S.; Wu, X. X.; Wang, G.; Lin, L. L.; Feng, X. M. Acta Chim. Sinica 2014, 72, 856(in Chinese).
      (谢明胜, 武晓霞, 王刚, 林丽丽, 冯小明, 化学学报, 2014, 72, 856.)
      (i) Zhou, R.; Xiao, W.; Yin, X.; Zhan, G.; Chen, Y. C. Acta Chim. Sinica 2014, 72, 862(in Chinese).
      (周容, 肖微, 尹祥, 詹固, 陈应春, 化学学报, 2014, 72, 862.)
      (j) Yang, L. J.; Ma, J. A. Acta Chim. Sinica 2016, 74, 130(in Chinese).
      (杨丽军, 马军安, 化学学报, 2016, 74, 130.)

    2. [2]

      Dochnahl, M.; Fu, G. C. Angew. Chem. Int. Ed. 2009, 48, 2391.  doi: 10.1002/anie.200805805

    3. [3]

      Wang, T.; Huang, X. L.; Ye, S. Org. Biomol. Chem. 2010, 8, 5007.  doi: 10.1039/c0ob00249f

    4. [4]

      Chatterjee, I.; Jana, C. K.; Steinmetz, M.; Grimme, S.; Studer, A. Adv. Synth. Catal. 2010, 352, 945.  doi: 10.1002/adsc.201000153

    5. [5]

      Kang, J. Y.; Bugarin, A.; Connell, B. T. Chem. Commun. 2008, 3522.

    6. [6]

      Yang, L.; Tan, B.; Wang, F.; Zhong, G. J. Org. Chem. 2009, 74, 1744.  doi: 10.1021/jo802515g

    7. [7]

      Chatterjee, I.; Fröhlich, R.; Studer, A. Angew. Chem., Int. Ed. 2011, 50, 11257.  doi: 10.1002/anie.v50.47

    8. [8]

      Chen, C. H.; Tsai, Y. C.; Liu, R. S. Angew. Chem., Int. Ed. 2013, 52, 4599.  doi: 10.1002/anie.201209850

    9. [9]

      Zhan, M.; Zhang, S.; Huang, Z.; Xi, Z. Chem. Asian J. 2015, 10, 862.  doi: 10.1002/asia.v10.4

    10. [10]

      Liu, R. S.; Ghorpade, S. M.; Jadhav, P. D. Chem. Eur. J. 2016, 22, 1  doi: 10.1002/chem.201504553

    11. [11]

      Arribas, C.; Carreño, M. C.; García-Ruano, J. L.; Rodríguez, J. F.; Santos, M.; Sanz-Tejedor, M. A. Org. Lett. 2000, 2, 3165.  doi: 10.1021/ol0063611

    12. [12]

      Miller, C. A; Batey, R. A. Org. Lett. 2004, 6, 699.  doi: 10.1021/ol0363117

    13. [13]

      Yamamoto, Y.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 4128.  doi: 10.1021/ja049849w

    14. [14]

      Calvet, G.; Guillot, R.; Blanchard, N.; Kouklovsky, C. Org. Biomol. Chem. 2005, 3, 4395.  doi: 10.1039/b513397a

    15. [15]

      Yamamoto, Y.; Yamamoto, H. Angew. Chem., Int. Ed. 2005, 44, 7082.  doi: 10.1002/(ISSN)1521-3773

    16. [16]

      Jana, C. K.; Studer, A. Angew. Chem., Int. Ed. 2007, 46, 6542.  doi: 10.1002/(ISSN)1521-3773

    17. [17]

      Jana, C. K.; Grimme, S.; Studer, A. Chem. Eur. J. 2009, 15, 9078.  doi: 10.1002/chem.v15:36

    18. [18]

      Monbaliu, J. C.; Marchand-Brynaert, J. Tetrahedron Lett. 2008, 49, 1839.  doi: 10.1016/j.tetlet.2008.01.050

    19. [19]

      Jana, C. K.; Studer, A. Chem. Eur. J. 2008, 14, 6326.  doi: 10.1002/chem.200800903

    20. [20]

      Yang, B.; Miller, P. A.; Möllmann, U.; Miller, M. J. Org. Lett. 2009, 11, 2828.  doi: 10.1021/ol900997t

    21. [21]

      Monbaliu, J. C.; Tinant, B.; Marchand-Brynaert, J. J. Org. Chem. 2010, 75, 5478.  doi: 10.1021/jo100230r

    22. [22]

      Monbaliu, J. C. M.; Cukalovic, A.; Marchand-Brynaert, J.; Stevens, C. V. Tetrahedron Lett. 2010, 51, 5830.  doi: 10.1016/j.tetlet.2010.08.117

    23. [23]

      Yang, B.; Zöllner, T.; Gebhardt, P.; Möllmann, U.; Miller, M. J. Org. Biomol. Chem. 2010, 8, 691.  doi: 10.1039/B922450E

    24. [24]

      Chaiyaveij, D.; Cleary, L.; Batsanov, A. S.; Marder, T. B.; Shea, K. J.; Whiting, A. Org. Lett. 2011, 13, 3442.  doi: 10.1021/ol201188d

    25. [25]

      Jenkins, N. E.; Ware Jr, R. W.; Atkinson, R. N.; King, S. B. Synth. Commun. 2000, 30, 947.  doi: 10.1080/00397910008087108

    26. [26]

      Flower, K. R.; Lightfoot, A. P.; Wan, H.; Whiting, A. J. Chem. Soc., Perkin Trans. 12002, 18, 2058.

    27. [27]

      Frazier, C. P.; Bugarin, A.; Engelking, J. R.; Read de Alaniz, J. Org. Lett. 2012, 14, 3620.  doi: 10.1021/ol301414k

    28. [28]

      Anand, A.; Bhargava, G.; Singh, P.; Mehra, S.; Kumar, V.; Mahajan, M. P.; Bisetty, K. Lett. Org. Chem. 2012, 9, 411.  doi: 10.2174/157017812801322444

    29. [29]

      Berti, F.; Di Bussolo, V.; Pineschi, M. J. Org. Chem. 2013, 78, 7324.  doi: 10.1021/jo4009996

    30. [30]

      Samoshin, A. V.; Hawker, C. J.; Read de Alaniz, J. ACS Macro Lett. 2014, 3, 753.  doi: 10.1021/mz500348y

    31. [31]

      Eberlin, L.; Carboni, B.; Whiting, A. J. Org. Chem. 2015, 80, 6574.  doi: 10.1021/acs.joc.5b00593

    32. [32]

      Chaiyaveij, D.; Batsanov, A. S.; Fox, M. A.; Marder, T. B.; Whiting, A. J. Org. Chem. 2015, 80, 9518.  doi: 10.1021/acs.joc.5b01470

    33. [33]

      Pous, J.; Courant, T.; Bernadat, G.; Iorga, B. I.; Blanchard, F.; Masson, G. J. Am. Chem. Soc. 2015, 137, 11950.  doi: 10.1021/jacs.5b08515

    34. [34]

      Maji, B.; Yamamoto, H. J. Am. Chem. Soc. 2015, 137, 15957.  doi: 10.1021/jacs.5b11273

    35. [35]

      Han, R.; Qi, J.; Gu, J.; Ma, D.; Xie, X.; She, X. ACS Catal. 2013, 3, 2705.  doi: 10.1021/cs400602v

    36. [36]

      Xu, Z. J.; Zhu, D.; Zeng, X.; Wang, F.; Tan, B.; Hou, Y.; Lv, Y.; Zhong, G. Chem. Commun. 2010, 46, 2504.  doi: 10.1039/b924575h

    37. [37]

      Reddy, A. R.; Guo, Z.; Siu, F. M.; Lok, C. N.; Liu, F.; Yeung, K. C.; Zhou, C. Y.; Che, C. M. Org. Biomol. Chem. 2012, 10, 9165.  doi: 10.1039/c2ob26518d

    38. [38]

      Molander, G. A.; Cavalcanti, L. N. Org. Lett. 2013, 15, 3166.  doi: 10.1021/ol401402d

    39. [39]

      Chen, H.; Wang, Z.; Zhang, Y.; Huang, Y. J. Org. Chem. 2013, 78, 3503.  doi: 10.1021/jo400215e

    40. [40]

      Reddy, A. R.; Zhou, C. Y.; Che, C. M. Org. Lett. 2014, 16, 1048.  doi: 10.1021/ol4035098

    41. [41]

      Pagar, V. V.; Liu, R. S. Angew. Chem., Int. Ed. 2015, 54, 4923.  doi: 10.1002/anie.201500340

    42. [42]

      Chakrabarty, S.; Chatterjee, I.; Wibbeling, B.; Daniliuc, C. G.; Studer, A. Angew. Chem., Int. Ed. 2014, 53, 5964.  doi: 10.1002/anie.201400885

    43. [43]

      Vemula, N., Stevens, A. C.; Schon, T. B.; Pagenkopf, B. L. Chem. Commun. 2014, 50, 1668.  doi: 10.1039/c3cc47775d

    44. [44]

      Vemula, N.; Pagenkopf, B. L. Eur. J. Org. Chem. 2015, 4900.

    45. [45]

      Suga, H.; Shi, X. L.; Ibata, T. Bull. Chem. Soc. Jpn. 1998, 71, 1231.  doi: 10.1246/bcsj.71.1231

    46. [46]

      Zhu, D.; Lu, M.; Chua, P. J.; Tan, B.; Wang, F.; Yang, X.; Zhong, G. Org. Lett. 2008, 10, 4585.  doi: 10.1021/ol801864c

    47. [47]

      Marwaha, A.; Singh, P.; Mahajan, M. P. Tetrahedron 2006, 62, 5474.  doi: 10.1016/j.tet.2006.03.047

    48. [48]

      de los Santos, J. M.; Ignacio, R.; Aparicio, D.; Palacios, F.; Ezpeleta, J. M. J. Org. Chem. 2009, 74, 3444.  doi: 10.1021/jo900489j

    49. [49]

      Kondacs, L. A.; Pilipecz, M. V.; Mucsi, Z.; Balázs, B.; Gáti, T.; Nyerges, M.; Dancsó, A.; Nemes, P. Eur. J. Org. Chem. 2015, 6872.  doi: 10.1021/jo010476g

    50. [50]

      Yoon, S. C.; Kim, K. J.; Park, Y. J. J. Org. Chem. 2001, 66, 7334.  doi: 10.1002/(ISSN)1099-0682

    51. [51]

      Shatzmiller, S.; Lidor, R.; Bahar, E.; Goldberg, I. Lebigs Ann. Chem. 1991, 851.

    52. [52]

      Paulini, K.; Reißig, H. U. Chem. Ber. 1994, 127, 685.  doi: 10.1002/(ISSN)1099-0682

    53. [53]

      de los Santos, J. M.; Ignacio, R.; Es Sbai, Z.; Aparicio, D.; Pa-lacios, F. J. Org. Chem. 2014, 79, 7607.  doi: 10.1021/jo501339c

    54. [54]

      Wabnitz, T. C.; Saaby, S.; Jørgensen, K. A. Org. Biomol. Chem. 2004, 2, 828.  doi: 10.1039/B316518C

    55. [55]

      Penoni, A.; Volkmann, J.; Nicholas, K. M. Org. Lett. 2002, 4, 699.  doi: 10.1021/ol017139e

    56. [56]

      Penoni, A.; Palmisano, G.; Broggini, G.; Kadowaki, A.; Nicholas, K. M. J. Org. Chem. 2006, 71, 823.  doi: 10.1021/jo051609r

    57. [57]

      Tibiletti, F.; Simonetti, M.; Nicholas, K. M.; Palmisano, G.; Parravicini, M.; Imbesi, F.; Tollari, S.; Penoni, A. Tetrahedron 2010, 66, 1280.  doi: 10.1016/j.tet.2009.12.020

    58. [58]

      Murru, S.; Gallo, A. A.; Srivastava, R. S. ACS Catal. 2010, 1, 29.

    59. [59]

      Murru, S.; Gallo, A. A.; Srivastava, R. S. Eur. J. Org. Chem. 2011, 2035.

    60. [60]

      Pagar, V. V.; Jadhav, A. M.; Liu, R. S. J. Am. Chem. Soc. 2011, 133, 20728.  doi: 10.1021/ja209980d

    61. [61]

      Otley, K. D.; Ellman, J. A. J. Org. Chem. 2014, 79, 8296.  doi: 10.1021/jo5015432

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