Citation: Wang Lianjun, Chi Yue, Zhang Wenxiong, Xi Zhenfeng. Transition-Metal-Catalyzed Guanylation Reaction of Amines with Carbodiimides Constructing Guanidines[J]. Chinese Journal of Organic Chemistry, ;2018, 38(6): 1341-1349. doi: 10.6023/cjoc201801037 shu

Transition-Metal-Catalyzed Guanylation Reaction of Amines with Carbodiimides Constructing Guanidines

  • Corresponding author: Zhang Wenxiong, wx_zhang@pku.edu.cn
  • Received Date: 26 January 2018
    Revised Date: 14 February 2018
    Available Online: 28 June 2018

    Fund Project: the National Natural Science Foundation of China 21725201the National Natural Science Foundation of China 21572005Project supported by the National Natural Science Foundation of China (Nos. 21725201, 21572005)

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  • Guanidine derivatives are an important class of nitrogen-containing organic compounds, which are widely used in various pharmaceuticals, agrochemicals, sweeteners, explosives, and so on. Although classical methods for the synthesis of guanidines are established, there are still many fatal shortcomings which need to be resolved. In recent years, it has been gradually turned to the direct catalytic guanylation reaction of amines with carbodiimides. In this paper, the recent progress in transition-metal-catalyzed guanylation reaction of amines with carbodiimides to construct acyclic or cyclic guanidines based on the catalytic reaction mechanism, reaction system, the scope of substrates, etc. is reviewed.
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    1. [1]

      (a) Berlinck, R. G. S. Nat. Prod. Rep. 1999, 16, 339.
      (b) Blondeau, P. ; Segura, M. ; Pérez-Fernández, R. ; de Mendoza, J. Chem. Soc. Rev. 2007, 36, 198.
      (c) Berlinck, R. G. S. ; Burtoloso, A. C. B. ; Kossuga, M. H. Nat. Prod. Rep. 2008, 25, 919.
      (d) Coles, M. P. Chem. Commun. 2009, 3659.
      (e) Berlinck, R. G. S. ; Burtoloso, A. C. B. ; Trindade-Silva, A. E. ; Romminger, S. ; Morais, R. P. ; Bandeira, K. ; Mizuno, C. M. Nat. Prod. Rep. 2010, 27, 1871.
      (f) Castagnolo, D. ; Schenone, S. ; Botta, M. Chem. Rev. 2011, 111, 5247.
      (g) Berlinck, R. G. S. ; Trindade-Silva, A. E. ; Santos, M. F. C. Nat. Prod. Rep. 2012, 29, 1382.
      (h) Berlinck, R. G. S. ; Trindade-Silva, A. E. ; Santos, M. F. C. Nat. Prod. Rep. 2012, 29, 1382.
      (i) Peng, K. ; Ding, W. ; Tu, W. ; Hu, J. ; Liu, C. ; Yang, J. Acta Chim. Sinica 2016, 74, 713(in Chinese).
      (彭开美, 丁伟, 涂伟萍, 胡剑青, Liu Chao, Yang Jian, 化学学报, 2016, 74, 713. )
      (j) Xu, X. ; Chen, X. ; Li, J. ; Xu, W. ; Zhang, Y. Chin. J. Org. Chem. 2016, 36, 1985(in Chinese).
      (徐树英, 陈小佳, 黎吉辉, 许文茸, 张玉苍, 有机化学, 2016, 36, 1985. )

    2. [2]

      (a) Selig, P. Synthesis 2013, 45, 703.
      (b) Fu, X. ; Tan, C. -H. Chem. Commun. 2011, 47, 8210.
      (c) Taylor, J. E. ; Bull, S. D. ; Williams, J. M. J. Chem. Soc. Rev. 2012, 41, 2109.

    3. [3]

      (a) Edelmann, F. T. Coord. Chem. Rev. 1994, 137, 403.
      (b) Zhou, Y. ; Yap, G. P. A. ; Richeson, D. S. Organometallics 1998, 17, 4387.
      (c) Luo, Y. ; Yao, Y. ; Shen, Q. Macromolecules 2002, 35, 8670.
      (d) Coles, M. P. Dalton Trans. 2006, 985.
      (e) Zhang, J. ; Zhou, X. C. R. Chim. 2010, 13, 633.
      (f) Zhang, J. ; Zhou, X. Dalton Trans. 2011, 40, 9637.

    4. [4]

      (a) Alonso-Moerno, C. ; Antiñolo, A. ; Carrillo-Hermosilla, F. ; Otero, A. Chem. Soc. Rev. 2014, 43, 3406.

    5. [5]

      Molina, P.; Aller, E.; Lorenzo, A. Synlett 2003, 714.
       

    6. [6]

      Ong, T.-G.; Yap, G. P. A.; Richeson, D. S. J. Am.Chem.Soc. 2003, 125, 8100.  doi: 10.1021/ja035716j

    7. [7]

      (a) Zhang, W. -X. ; Nishiura, M. ; Hou, Z. Synlett 2006, 1213.
      (b) Zhang, W. -X. ; Nishiura, M. ; Hou, Z. Chem. Eur. J. 2007, 13, 4307.
      (c) Zhang, W. -X. ; Hou, Z. Org. Biomol. Chem. 2008, 6, 1720.
      (d) Suzuki, T. ; Zhang, W. -X. ; Nishiura, M. ; Hou, Z. J. Synth. Org. Chem. Jpn. 2009, 67, 451.
      (e) Nishiura, M. ; Hou, Z. Bull. Chem. Soc. Jpn. 2010, 83, 595.

    8. [8]

      (a) Zhang, W. -X. ; Xu, L. ; Xi, Z. Chem. Commun. 2015, 51, 254.
      (b) Xu, L. ; Zhang, W. -X. ; Xi, Z. Organometallics 2015, 34, 1787.
      (c) Chi, Y. ; Xu, L. ; Du, S. ; Yan, H. ; Zhang, W. -X. ; Xi, Z. Chem. Eur. J. 2015, 21, 10369.
      (d) Zhang, W. -X. ; Li, D. ; Wang, Z. ; Xi, Z. Organometallics 2009, 28, 882.

    9. [9]

      (a) Du, Z. ; Li, W. ; Zhu, X. ; Xu, F. ; Shen, Q. J. Org. Chem. 2008, 73, 8966.
      (b) Zhu, X. ; Du, Z. ; Xu, F. ; Shen, Q. J. Org. Chem. 2009, 74, 6347.
      (c) Cao, Y. ; Du, Z. ; Li, W. ; Li, J. ; Zhang, Y. ; Xu, F. ; Shen, Q. Inorg. Chem. 2011, 50, 3729.
      (d) Li, Z. ; Xue, M. ; Yao, H. Sun, H. ; Zhang, Y. Shen, Q. J. Organomet. Chem. 2012, 713, 27.
      (e) Cai, L. ; Yao, Y. ; Xue, M. ; Zhang, Y. ; Shen, Q. Appl. Organomet. Chem. 2013, 27, 366.
      (f) Tu, J. ; Li, W. ; Xue, M. ; Zhang, Y. ; Shen, Q. Dalton Trans. 2013, 42, 5890.

    10. [10]

      (a) Liu, C. ; Zhou, S. ; Wang, S. ; Zhang, L. ; Yang, G. Dalton Trans. 2010, 39, 8994.
      (b) Wu, Y. ; Wang, S. ; Zhang, L. ; Yang, G. ; Zhu, X. ; Zhou, Z. ; Zhu, H. ; Wu, S. Eur. J. Org. Chem. 2010, 326.

    11. [11]

      (a) Shen, H. ; Chan, H. -S. ; Xie, Z. Organometallics 2006, 25, 5515.
      (b) Shen, H. ; Xie, Z. J. Organomet. Chem. 2009, 694, 1652.
      (c) Shen, H. ; Wang, Y. ; Xie, Z. Org. Lett. 2011, 13, 4562.

    12. [12]

      Schweizer, P. D.; Wadepohl, H.; Gade, L. H. Oganometallics 2013, 32, 3697.  doi: 10.1021/om400323p

    13. [13]

      Montilla, F.; Pastor, A.; Galindo, A. J.Organomet.Chem. 2004, 689, 993.  doi: 10.1016/j.jorganchem.2004.01.005

    14. [14]

      Romero-Fernández, J.; Carrillo-Hermosilla, F.; Antiñolo, A.; Alonso-Moreno, C.; Rodríguez, A. M.; López-Solera, I.; Otero, A. Dalton Trans. 2010, 39, 6419.  doi: 10.1039/c0dt00064g

    15. [15]

      Montilla, F.; del Río, D.; Pastor, A.; Galindo, A. Organometallics 2006, 25, 4996.  doi: 10.1021/om060535m

    16. [16]

      Mukherjee, A.; Sen, T. K.; Mandal, S. K.; Maity, B.; Koley, D. RSC Adv. 2013, 3, 1255.  doi: 10.1039/C2RA21778C

    17. [17]

      Elorriaga, D.; Carrillo-Hermosilla, F.; Antiñolo, A.; Suά;rea, F. J.; López-Solera, I.; Fernά;ndez-Galά;n, R.; Villaenño, E. Dalton Trans. 2013, 42, 8223.  doi: 10.1039/c3dt50477h

    18. [18]

      (a) Li, D. ; Guang, J. ; Zhang, W. -X. ; Wang, Y. ; Xi, Z. Org. Biomol. Chem. 2010, 8, 1816.
      (b) Li, D. ; Wang, Y. ; Zhang, W. -X. ; Zhang, S. ; Guang, J. ; Xi, Z. Organometallics 2011, 30, 5278.

    19. [19]

      (a) Alonso-Moreno, C. ; Carrillo-Hermosilla, F. ; Garcés, A. ; Otero, A. ; López-Solera, I. ; Rodríguez, A. M. ; Antiñolo, A. Organometallics 2010, 29, 2789.
      (b) Bravo, I. ; Alonso-Moreno, C. ; Posadas, I. ; Albaladejo, J. ; Carrillo-Hermosilla, F. ; Ceña, V. ; Garzón, A. ; López-Solera, I. ; Romero-Castillo, L. RSC Adv. 2016, 6, 8267.

    20. [20]

      Bhattacharjee, J.; Sachdeva, M.; Banerjee, I.; Panda, T. K. J. Chem.Sci. 2016, 128, 875.  doi: 10.1007/s12039-016-1096-y

    21. [21]

      Kantam, M. L.; Priyadarshini, S.; Joseph, P. J. A.; Srinivas, P.; Vinu, A.; Klabunde, K. J.; Nishina, Y. Tetrahedron 2012, 68, 5730.  doi: 10.1016/j.tet.2012.05.044

    22. [22]

      Pottabathula, S.; Royo, B. Tetrahedron Lett. 2012, 53, 5156.  doi: 10.1016/j.tetlet.2012.07.065

    23. [23]

      Tan, D.; Mottillo, C.; Katsenis, A. D.; Štrukil, V.; Friščić, T. Angew. Chem., Int.Ed. 2014, 126, 9475.  doi: 10.1002/ange.201404120

    24. [24]

      Grirrane, A.; Garcia, H.; Corma, A.; Álvarez, E.Chem. Eur.J. 2012, 18, 14934.  doi: 10.1002/chem.v18.47

    25. [25]

      Grirrane, A.; Garcia, H.; Álvarez, E. Beilstein J.Org. Chem. 2013, 9, 1455.  doi: 10.3762/bjoc.9.165

    26. [26]

      Tayama, E.; Ishikawa, M.; Iwamoto, H.; Hasegawa, E. Tetrahedron Lett. 2012, 53, 5159.  doi: 10.1016/j.tetlet.2012.07.070

    27. [27]

      Yavari, I.; Sodagar, E.; Nematpour, M.; Askarian-Amiri, M. Synlett 2015, 26, 1230.  doi: 10.1055/s-00000083

    28. [28]

      Frindy, S.; Kadib, A. E.; Lahcini, M.; Primo, A.; García, H. ACS Catal. 2016, 6, 3863.  doi: 10.1021/acscatal.6b00995

    29. [29]

      (a) Rauws, T. R. M. ; Maes, B. U. W. Chem. Soc. Rev. 2012, 41, 2463.
      (b) Mulcahy, J. V. ; Bois, J. D. J. Am. Chem. Soc. 2008, 130, 12630.
      (c) Aron, Z. D. ; Overman, L. E. Chem. Commun. 2004, 253.
      (d) Gainer, M. J. ; Bennett, N. R. ; Takahashi, Y. ; Looper, R. E. Angew. Chem., Int. Ed. 2011, 50, 684.

    30. [30]

      (a) Ishikawa, T. ; Kumamoto, T. Synthesis 2006, 737.
      (b) Heys, L. ; Moore, C. G. ; Murphy, P. J. Chem. Soc. Rev. 2000, 29, 57.

    31. [31]

      (a) Schmuck, C. Coord. Chem. Rev. 2006, 250, 3053.
      (b) Edelmann, F. T. Chem. Soc. Rev. 2012, 41, 7657.
      (c) Turočkin, A. ; Honeker, R. ; Raven, W. ; Selig, P. J. Org. Chem. 2016, 81, 4516.

    32. [32]

      (a) Isobe, T. ; Fukuda, K. ; Tokunaga, T. ; Seki, H. ; Yamaguchi, K. ; Ishikawa, T. J. Org. Chem. 2000, 65, 7774.
      (b) Butler, D. C. D. ; Inman, G. A. ; Alper, H. J. Org. Chem. 2000, 65, 5887.
      (c) Heinelt, U. ; Schultheis, D. ; Jäger, S. ; Lindenmaier, M. ; Pollex, A. ; Beckmann, H. S. G. Tetrahedron 2004, 60, 9883.
      (d) Berlinck, R. G. S. ; Kossuga, M. H. Nat. Prod. Rep. 2005, 22, 516.
      (e) Kim, M. ; Mulcahy, J. V. ; Espino, C. G. ; Bois, J. D. Org. Lett. 2006, 8, 1073.
      (f) Blackburn, C. ; Achab, A. ; Elder, A. ; Ghosh, S. ; Guo, J. ; Harriman, G. ; Jones, M. J. Org. Chem. 2005, 70, 10206.
      (g) Hirota, S. ; Kato, R. ; Suzuki, M. ; Soneta, Y. ; Otani, T. ; Saito, T. Eur. J. Org. Chem. 2008, 2075.

    33. [33]

      (a) Lv, X. ; Bao, W. J. Org. Chem. 2009, 74, 5618.
      (b) He, H. -F. ; Wang, Z. -J. ; Bao, W. Adv. Synth. Catal. 2010, 352, 2905.
      (c) Yuan, G. ; Liu, H. ; Gao, J. ; Xu, H. ; Jiang, L. ; Wang, X. ; Lv, X. RSC Adv. 2014, 4, 21904.
      (d) Xu, B. ; Peng, B. ; Cai, B. ; Wang, S. ; Wang, X. ; Lv, X. Adv. Synth. Catal. 2016, 358, 653.

    34. [34]

      (a) Evindar, G. ; Batey, R. A. Org. Lett. 2003, 5, 133.
      (b) Deng, X. ; McAllister, H. ; Mani, N. S. J. Org. Chem. 2009, 74, 5742.
      (c) Saha, P. ; Ramana, T. ; Purkait, N. ; Ali, M. A. ; Paul, R. ; Punniyamurthy, T. J. Org. Chem. 2009, 74, 8719.
      (d) Yuan, G. ; Liu, H. ; Gao, J. ; Yang, K. ; Niu, Q. ; Mao, H. ; Wang, X. ; Lv, X. J. Org. Chem. 2014, 79, 1749.
      (e) Chi, Y. ; Zhang, W. -X. ; Xi, Z. Org. Lett. 2014, 16, 6274.

    35. [35]

      Wang, F.; Cai, S.; Liao, Q.; Xi, C. J.Org.Chem. 2011, 76, 3174.  doi: 10.1021/jo200014v

    36. [36]

      (a) Zeng, F. ; Alper, H. Org. Lett. 2010, 12, 1188.
      (b) Zeng, F. ; Alper, H. Org. Lett. 2010, 12, 3642.

    37. [37]

      Roberts, B.; Liptrot, D.; Luker, T.; Stocks, M. J.; Barber, C.; Webb, N.; Dods, R.; Martin, B. Tetrahedron Lett. 2011, 52, 3793.  doi: 10.1016/j.tetlet.2011.05.052

    38. [38]

      Qiu, G.; Liu, G.; Pu, S.; Wu, J. Chem.Commun. 2012, 48, 2903.  doi: 10.1039/c2cc18001d

    39. [39]

      Shen, H.; Wang, Y.; Xie, Z. Org.Lett. 2011, 13, 4562.  doi: 10.1021/ol201752e

    40. [40]

      Baishya, A.; Peddarao, T.; Barman, M. K.; Nembenna, S. New J. Chem. 2015, 39, 7503.  doi: 10.1039/C5NJ01612F

    41. [41]

      Penafiel, J. ; Maron, L. ; Harder, S. Angew. Chem., Int. Ed. 2015, 54, 201.
      Wangngae, S. ; Pattarawarapan, M. ; Phakhodee, W. Synlett 2016, 27, 1121.

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