Citation: Xu Xin-Ming, Chen De-Mao, Wang Zu-Li. Recent advances in sulfenylation of C(sp3)-H bond under transition metal-free conditions[J]. Chinese Chemical Letters, ;2020, 31(1): 49-57. doi: 10.1016/j.cclet.2019.05.048 shu

Recent advances in sulfenylation of C(sp3)-H bond under transition metal-free conditions

  • Received Date: 18 April 2019
    Revised Date: 14 May 2019
    Accepted Date: 23 May 2019
    Available Online: 25 January 2019

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  • In recent years, the transition metal-free sulfenylation of C-H bond for C-S formation has been rapidly advanced and has become an eco-friendly synthetic tool for pharmacists and organic chemists. Various natural or bioactive molecules such as (hetero)arenes, olefins, carbonyl compounds, alkanes, have been employed for sulfenylating reactions. This review will focus on the recent five-year advances in C-S bond formation via direct sulfenylation of C(sp3)-H bonds under metal-free conditions and elaborate their mechanisms from a new perspective.
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    1. [1]

      (a) R.J. Cremlyn, An Introduction to Organosulfur Chemistry, Wiley, New York, 1996;
      (b) D. Meng, W. Chen, W. Zhao, J. Nat. Prod. 70 (2007) 824-829;
      (c) M. Kvasnika, M. Urban, N.J. Dickinson, J. Sarek, Nat. Prod. Rep. 32 (2015) 1303-1330.

    2. [2]

      M.H. Feng, B.Q. Tang, H.L. Steven, X.F. Jiang, Curr. Top. Med. Chem. 16(2016) 1200-1216.  doi: 10.2174/1568026615666150915111741

    3. [3]

      (a) D.A. Boyd, Angew. Chem. Int. Ed. 55 (2016) 15486-15502;
      (b) D. Wu, W. Pisula, M.C. Haberecht, X. Feng, K. Müllen, Org. Lett. 11 (2009) 5686-5689;
      (c) S.M. Yang, J.J. Shie, J.M. Fang, S.K. Nandy, Y.Y. Chang, J. Org. Chem. 67 (2002) 52085215.

    4. [4]

      (a) J.C. Carretero, Chem. Commun. 47(2011) 2207-2211;
      (b) H. Pellisier, Chiral Sulfur Ligands in Asymmetric Catalysis, RSC Catalysis Series 2, Cambridge, 2009.

    5. [5]

      (a) A. Kausar, S. Zulfiqar, M.I. Sarwar, Pol. Rev. 54 (2014) 185-267;
      (b) A.S. Rahate, K.R. Nemade, S.A. Waghuley, Rev. Chem. Eng. 29 (2013) 471-489;
      (c) N. Spassky, Phosphorus Sulfur Silicon Relat. Elem. 74 (1993) 71-92.

    6. [6]

      (a) J.F. Hartwig, Nature 455 (2008) 314-322;
      (b) Q. Lu, J. Zhang, F.L. Wei, et al., Angew. Chem. Int. Ed. 52 (2013) 7156-7159;
      (c) Q.Q. Lu, J. Zhang, G.L. Zhao, et al., J. Am. Chem. Soc.135 (2013) 11481-11484;
      (d) S.H. Hao, L.X. Li, D.Q. Dong, Z.L. Wang, Chin. J. Catal. 38 (2017) 1664-1667;
      (e) L.H. Lu, S.J. Zhou, W.B. He, et al., Org. Biomol. Chem. 16 (2018) 9064-9068;
      (f) L.Y. Xie, Y.J. Li, J. Qu, et al., Green Chem. 19 (2017) 5642-5646;
      (g) F.L. Zeng, X.L. Chen, S.Q. He, et al., Org. Chem. Front. 6 (2019) 1476-1480;
      (h) D. Yang, P. Sun, W. Wei, et al., Chem. -Eur. J. 24 (2018) 4423-4427;
      (i) L. Penga, Z. Hua, Z. Tang, Y. Jiao, X. Xu, Chin. Chem. Lett. 30 (2019) 1481-1487.

    7. [7]

      (a) M. Martinek, M. Korf, J. Srogl, Chem. Commun. 46 (2010) 4387-4389;
      (b) S.K. Sahoo, A. Banerjee, S. Chakraborty, B.K. Patel, ACS Catal. 2 (2012) 544-551;
      (c) O. Saidi, J. Marafie, A.E. Ledger, et al., J. Am. Chem. Soc. 133 (2011) 19298-19301;
      (d) N. Umierski, G. Manolikakes, Org. Lett. 15 (2013) 4972-4975;
      (e) Z. Wu, H. Song, X. Cui, et al., Org. Lett. 15 (2013) 1270-1273;
      (f) B. Niu, L. Xu, P. Xie, et al., ACS Comb. Sci. 16 (2014) 454-458.

    8. [8]

      (a) S.N. Zhang, S.H. Yang, L.H. Huang, et al., Chin. J. Org. Chem. 35 (2015) 2259-2274;
      (b) R. Chitrakar, A. Subbarayappa, Chem. Rec. 17 (2017) 1;
      (c) Y.Y. Liu, J. Xiong, L. Wei, Chin. J. Org. Chem. 37 (2017) 1667-1680;
      (d) D.Q. Dong, S.H. Hao, D.S. Yang, L.X. Li, Z.L. Wang, Eur. J. Org. Chem. 2017 (2017) 6576-6592;
      (e) L. Li, Y.Q. Ding, Mini-Rev. Org. Chem. 14 (2017) 407-418;
      (f) R. Dalpozzo, Org. Chem. Front. 4 (2017) 2063-2078;
      (g) M. Freckleton, A. Baeza, L. Benavent, R. Chinchilla, Asian. J. Org. Chem. 7 (2018) 1006-1014;
      (h) C.A. Jin, Q. Xu, G.F. Feng, Y. Jin, L.Y. Zahng, Chin. J. Org. Chem. 38 (2018) 775-790.

    9. [9]

      (a) A. Ghaderi, Tetrahedron 72 (2016) 4758-4782;
      (b) K.L. Dunbar, D.H. Scharf, A. Litomska, C. Hertweck, Chem. Rev. 117 (2017) 5521-5577;
      (c) J. Zhu, W.C. Yang, X.D. Wang, L. Wu, Adv. Synth. Catal. 360 (2018) 386-400;
      (d) Y. Luo, Y. Ma, Z. Hou, J. Am. Chem. Soc. 140 (2018) 114-117.

    10. [10]

      B.V. Varun, K. Gadde, K.R. Prabhu, Org. Lett. 17(2015) 2944-2947.  doi: 10.1021/acs.orglett.5b01221

    11. [11]

      H. Cao, J. Yuan, C. Liu, X.Q. Hu, A.W. Lei, RSC Adv. 5(2015) 41493-41496.  doi: 10.1039/C5RA04906G

    12. [12]

      Y. Jiang, J.X. Zou, L.T. Huang, et al., Org. Biomol. Chem. 16(2018) 1641-1645.  doi: 10.1039/C8OB00080H

    13. [13]

      Q. Chen, X. Wang, C. Wen, et al., RSC Adv. 7(2017) 39758-39761.  doi: 10.1039/C7RA06904A

    14. [14]

      Y. Liu, S.S. Badsara, Y. Liu, C. Lee, RSC Adv. 5(2015) 44299-44305.  doi: 10.1039/C5RA07204B

    15. [15]

      R. Rahaman, N. Devi, P. Barman, Tetrahedron Lett. 56(2015) 4224-4227.  doi: 10.1016/j.tetlet.2015.05.062

    16. [16]

      N. Devi, R. Rahaman, K. Sarma, P. Barman, Eur. J. Org. Chem. 2016(2016) 384-388.  doi: 10.1002/ejoc.201501148

    17. [17]

      B.M. Trost, Chem. Rev. 78(1978) 363-382.  doi: 10.1021/cr60314a002

    18. [18]

      B. Hu, Q. Zhang, S. Zhao, et al., Adv. Synth. Catal. 361(2019) 49-54.  doi: 10.1002/adsc.201801138

    19. [19]

      Y. Siddaraju, K.R. Prabhu, Org. Lett. 18(2016) 6090-6093.  doi: 10.1021/acs.orglett.6b03084

    20. [20]

      Y. Siddaraju, K.R. Prabhu, J. Org. Chem. 83(2018) 2986-2992.  doi: 10.1021/acs.joc.7b03290

    21. [21]

      Y. Siddaraju, K.R. Prabhu, Org. Biomol. Chem. 15(2017) 5191-5196.  doi: 10.1039/C7OB00561J

    22. [22]

      N. Devi, R. Rahaman, K. Sarma, T. Khan, P. Barman, Eur. J. Org. Chem. 2017(2017) 1520-1525.

    23. [23]

      (a) P.N. Kalaria, S.P. Satasia, J.R. Avalani, D.K. Raval, Eur. J. Med. Chem. 83 (2014) 655-664;
      (b) S.C. Karad, V.B. Purohit, D.K. Raval, Eur. J. Med. Chem. 84 (2014) 51-58.

    24. [24]

      R.D. Kamani, V.B. Purohit, R.P. Thummar, et al., ChemistrySelect 2(2017) 9670-9673.  doi: 10.1002/slct.201701924

    25. [25]

      (a) H. Jin, W. Wang, Z. Yang, et al., Heterocycles 96 (2018) 1786-1794;
      (b) X. Zhao, X. Lu, A. Wei, et al., Tetrahedron Lett. 57 (2016) 5330-5333;
      (c) X. Zhao, A. Wei, X. Lu, K. Lu, Molecules 22 (2017) 1208-1219.

    26. [26]

      X. Liu, H. Cui, D. Yang, et al., RSC Adv. 6(2016) 51830-51833.  doi: 10.1039/C6RA09739A

    27. [27]

      Q. Chen, Y. Huang, X. Wang, et al., Tetrahedron Lett. 58(2017) 3928-3931.  doi: 10.1016/j.tetlet.2017.08.067

    28. [28]

      (a) A.F. Vaquer, A. Frongia, F. Secci, E. Tuveri, RSC Adv. 5 (2015) 96695-96704;
      (b) H.W. Noh, C. Lee, H.Y. Jang, Bull. Korean Chem. Soc. 38 (2017) 389-391;
      (c) J.Q. Zhao, S.W. Luo, X.M. Zhang, et al., Tetrahedron 73 (2017) 5444-5450.

    29. [29]

      Y. Li, F. Zhu, Z. Wang, X.F. Wu, Chem. -Asian J. 11(2016) 3503-3507.  doi: 10.1002/asia.201601376

    30. [30]

      D. Wang, Z. Liu, Z. Wang, X. Ma, P. Yu, Green Chem. 21(2019) 157-163.  doi: 10.1039/C8GC03072C

    31. [31]

      Y. Liu, X. Yuan, K. Su, Y. Tian, B. Chen, Eur. J. Org. Chem. 2019(2019) 1649-1652.  doi: 10.1002/ejoc.201801806

    32. [32]

      Q. Chen, G. Yu, X. Wang, Y. Ou, Y. Huo, Green Chem. 21(2019) 798-802.  doi: 10.1039/C8GC03898H

    33. [33]

      S.K. Ayer, J.L. Roizen, J. Org. Chem. 84(2019) 3508-3523.  doi: 10.1021/acs.joc.9b00105

    34. [34]

      K. Liao, F. Zhou, J. Yu, W. Gao, J. Zhou, Chem. Commun. 51(2015) 16255-16258.  doi: 10.1039/C5CC07010D

    35. [35]

      L. Huang, J. Li, Y. Zhao, et al., J. Org. Chem. 80(2015) 8933-8941.  doi: 10.1021/acs.joc.5b01606

    36. [36]

      Y. You, Z. Wu, Z. Wang, et al., J. Org. Chem. 80(2015) 8470-8477.  doi: 10.1021/acs.joc.5b01491

    37. [37]

      X. Gao, J. Han, L. Wang, Synthesis 48(2016) 2603-2611.  doi: 10.1055/s-0035-1560435

    38. [38]

      Y. E, T. Yuan, L. Yin, Y. Xu, Tetrahedron Lett. 58(2017) 2521-2524.  doi: 10.1016/j.tetlet.2017.05.015

    39. [39]

      S.J. Singha Roy, S. Mukherjee, Org. Biomol. Chem. 15(2017) 6921-6925.  doi: 10.1039/C7OB01714F

    40. [40]

      J. Han, Y. Zhang, X.Y. Wu, H.N.C. Wong, Chem. Commun. 55(2019) 397-400.  doi: 10.1039/C8CC09049A

    41. [41]

      L. Cui, Y. You, X. Mi, S. Luo, Org. Chem. Front. 5(2018) 2313-2316.  doi: 10.1039/C8QO00496J

    42. [42]

      K. Nagata, D. Sano, O. Aoyama, et al., Heterocycles 92(2016) 631-635.  doi: 10.3987/COM-16-13414

    43. [43]

      F. Rota, L. Benhamou, T.D. Sheppard, Synlett 27(2016) 33-36.  doi: 10.1055/s-0035-1560769

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