Citation: Fu-Hua Qin, Xun-Jie Huang, Yi Liu, Hongze Liang, Qiang Li, Zhong Cao, Wen-Ting Wei, Wei-Min He. Alcohols controlled selective radical cyclization of 1, 6-dienes under mild conditions[J]. Chinese Chemical Letters, ;2020, 31(12): 3267-3270. doi: 10.1016/j.cclet.2020.04.042 shu

Alcohols controlled selective radical cyclization of 1, 6-dienes under mild conditions

    * Corresponding authors.
    E-mail addresses: (W.T. Wei) (W.M. He).
  • Received Date: 27 March 2020
    Revised Date: 20 April 2020
    Accepted Date: 20 April 2020
    Available Online: 15 December 2020


  • An efficient procedure for the selective preparation of hydroxy-, carbonyl- and acetal-containing 2-pyrrolidinones has been developed through radical cyclization of 1, 6-dienes initiated by α-C(sp3)-H functionalization of alcohols. This protocol could be conducted at catalyst-free conditions at relatively low temperature (80 ℃) by employing commercially available tert-butyl peroxybenzoate (TBPB) as the oxidant.
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    1. [1]

      (a) L. Ping, D.S. Chung, J. Bouffard, S.G. Lee, Chem. Soc. Rev. 46(2017) 4299-4328;
      (b) J.B. Peng, X.F. Wu, Angew. Chem. Int. Ed. 57(2018) 2-11;
      (c) J. Mahatthananchai, A.M. Dumas, J.W. Bode, Angew. Chem. Int. Ed. 51(2012) 10954-10990;
      (d) Y. Wei, M. Shi, ACS Catal. 6(2016) 2515-2524;
      (e) Z. Cao, Q. Zhu, Y.W. Lin, W.M. He, Chin. Chem. Lett. 30(2019) 2132-2138;
      (f) K.J. Liu, T.Y. Zeng, J.L. Zeng, et al., Chin. Chem. Lett. 30(2019) 2304-2308;
      (g) P. Bao, H. Yue, N. Meng, et al., Org. Lett. 21(2019) 7218-7222;
      (h) P. Bao, N. Meng, Y. Lv, et al., Org. Chem. Front. 6(2019) 3983-3988.

    2. [2]

      (a) Y. Hayashi, Chem. Sci. 7(2016) 866-880;
      (b) J. Sun, Y. Li, Y. Gui, et al., Chin. Chem. Lett. 30(2019) 569-572;
      (c) H.P. Zhao, G.C. Liang, S.M. Nie, et al., Green Chem. 22(2020) 404-410;
      (d) H.Y. Bi, M. Du, C.X. Pan, et al., J. Org. Chem. 84(2019) 9859-9868;
      (e) L.H. Lu, Z. Wang, W. Xia, et al., Chin. Chem. Lett. 30(2019) 1237-1240;
      (f) Q. Huang, L. Zhu, D. Yi, X. Zhao, W. Wei, Chin. Chem. Lett. 31(2020) 373-376;
      (g) Y. Zhang, K. Sun, Q. Lv, et al., Chin. Chem. Lett. 30(2019) 1361-1368;
      (h) C.H. Xu, Y. Li, J.H. Li, J.N. Xiang, W. Deng, Sci. China Chem. 62(2019) 1463-1475;
      (i) K. Sun, Y.F. Si, X.L. Chen, et al., Adv. Synth. Catal. 361(2019) 4483-4488.

    3. [3]

      (a) G.C. Lloyd-Jones, Org. Biomol. Chem. 1(2003) 215-236;
      (b) Z. Wang, W.-M. He, Chin. J. Org. Chem. 39(2019) 3594-3595;
      (c) Y. Liu, X.-L. Chen, K. Sun, et al., Org. Lett. 21(2019) 4019-4024;
      (d) Q.S. Zhao, G.Q. Xu, H. Liang, Z.Y. Wang, P.F. Xu, Org. Lett. 21(2019) 8615-8619;
      (e) G. Li, Q. Yan, X. Gong, X. Dou, D. Yang, ACS Sustainable Chem. Eng. 7(2019) 14009-14015;
      (f) Z. Shen, C. Pi, X. Cui, Y. Wu, Chin. Chem. Lett. 30(2019) 1374-1378;
      (g) X. Mi, Y. Kong, J. Zhang, C. Pi, X. Cui, Chin. Chem. Lett. 30(2019) 2295-2298;
      (h) Q.Q. Han, G.H. Li, Y.Y. Sun, et al., Tetrahedron Lett. (2020) 151704;
      (i) K. Sun, X.L. Chen, Y.L. Zhang, et al., Chem. Commun. (Camb.) 55(2019) 12615-12618.

    4. [4]

      (a) S.R. Guo, P.S. Kumar, M.H. Yang, Adv. Synth. Catal. 359(2016) 2-25;
      (b) S.Y. Zhang, F.M. Zhang, Y.Q. Tu, Chem. Soc. Rev. 40(2011) 1937-1949;
      (c) M.K. Lakshman, P.K. Vuram, Chem. Sci. 8(2017) 5845-5888.

    5. [5]

      (a) Y. Meng, L.N. Guo, H. Wang, X.H. Duan, Chem. Commun. (Camb.) 49(2013) 7540-7542;
      (b) Z.Z. Zhou, H.L. Hua, J.Y. Luo, et al., Tetrahedron 69(2013) 10030-10035;
      (c) W. Zhou, S.Y. Ni, H.B. Mei, J.L. Han, Y. Pan, Org. Lett. 17(2015) 2724-2727;
      (d) X.H. Ouyang, R.J. Song, J.H. Li, Eur. J. Org. Chem. 16(2014) 3395-3401.

    6. [6]

      (a) Y.N. Meng, Q.Q. Kang, T.T. Cao, et al., ACS Sustainable Chem. Eng. 7(2019) 18738-18743;
      (b) W.T. Wei, W.W. Ying, W.H. Bao, et al., ACS Sustainable Chem. Eng. 6(2018) 15301-15305;
      (c) X.D. Xu, T.T. Cao, Y.N. Meng, et al., ACS Sustainable Chem. Eng. 7(2019) 13491-13496;
      (d) X.X. Meng, Q.Q. Kang, J.Y. Zhang, et al., Green Chem. 22(2020) 1388-1392;
      (e) W.B. He, L.Q. Gao, X.J. Chen, et al., Chin. Chem. Lett. 31(2020) 1895-1898;
      (f) W.H. Bao, Z. Wang, X. Tang, et al., Chin. Chem. Lett. 30(2019) 2259-2262;
      (g) S. Peng, Y.X. Song, J.Y. He, et al., Chin. Chem. Lett. 30(2019) 2287-2290.

    7. [7]

      (a) G. Martinez-Ariza, M. Ayaz, S.A. Roberts, et al., Angew. Chem. Int. Ed. 54(2015) 11672-11676;
      (b) X.L. Du, D.W. Yin, Z.M. Ge, X. Wang, R.T. Li, RSC Adv. 7(2017) 24547-24550;
      (c) J.C. Anderson, L.R. Horsfall, A.S. Kalogirou, et al., J. Org. Chem. 77(2012) 6186-6198;
      (d) D. Yang, G.Y. Lian, H.F. Yang, et al., J. Org. Chem. 74(2009) 8610-8615.

    8. [8]

      (a) J.H. Fu, J.W. Yuan, Y. Zhang, et al., Org. Chem. Front. 5(2018) 3382-3390;
      (b) D.Q. Xue, H. Chen, Y.L. Xu, et al., Org. Biomol. Chem.165(2017) 10044-10052.

    9. [9]

      X.X. Meng, T.T. Cao, S.Z. Song, et al., Asian J. Org. Chem. 8(2019) 1827-1829.

  • 加载中
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    沈阳化工大学材料科学与工程学院 沈阳 110142

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