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2023 , Vol. 43 >Issue 3: 1102 - 1114

DOI: https://doi.org/10.6023/cjoc202212032

研究论文

可见光催化合成二氟烷基取代的多环吲哚化合物

  • 赵金晓 ,
  • 魏彤辉 ,
  • 柯森 ,
  • 李毅
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  • 福州大学化学学院 福州 350108

收稿日期: 2022-12-26

  修回日期: 2023-02-17

  网络出版日期: 2023-02-23

基金资助

国家自然科学基金(21871049)

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Visible Light-Catalyzed Synthesis of Difluoroalkylated Polycyclic Indoles

  • Jinxiao Zhao ,
  • Tonghui Wei ,
  • Sen Ke ,
  • Yi Li
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  • College of Chemistry, Fuzhou University, Fuzhou 350108
* Corresponding author. E-mail:

Received date: 2022-12-26

  Revised date: 2023-02-17

  Online published: 2023-02-23

Supported by

National Natural Science Foundation of China(21871049)

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摘要

多环吲哚分子广泛地存在于天然产物和药物分子中, 并且在医药农药和染料工业上有着广泛的应用. 尽管目前合成吲哚多环类化合物的方法已经取得相当的发展, 但探索更高效、更温和的合成高度官能团化的吲哚多环类化合物的实验策略依然具有重要的科研意义与价值. 在可见光催化条件下, 以二氟烷基溴化物作为氟源, 3-吲哚烯烃类化合物作为底物, 通过自由基串联环化反应, 一步合成了具有季碳中心的二氟烷基吲哚类化合物. 该方法操作简单, 条件温和, 底物适应范围广泛, 产物收率良好, 为含氟的多环吲哚化合物提供了绿色、高效的合成路径.

关键词： 可见光催化; 多环吲哚; 自由基反应; 二氟烷基化; 串联环化

本文引用格式

赵金晓 , 魏彤辉 , 柯森 , 李毅 . 可见光催化合成二氟烷基取代的多环吲哚化合物[J]. 有机化学, 2023 , 43(3) : 1102 -1114 . DOI: 10.6023/cjoc202212032

Abstract

Polycyclic indoles are widely found in natural products and pharmaceutical molecules, and have a wide range of applications in the pharmaceutical, pesticide and dye industries. Although considerable development has been made in the synthesis of indole polycycles, it is still of great scientific interest and value to explore more efficient and milder experimental strategies for the synthesis of highly-functionalized polycyclic indoles. Herein, a one-step radical tandem cyclization reaction to synthesize difluoroalkylindoles with quaternary carbon centers by using difluorobromoesters as the fluorine source and 3-alkenyl indoles as the substrates under visible light-catalyzed conditions was developed. The method is easy-to-operate and mild in conditions, with a wide range of substrate adaptability and good yields, providing a green and efficient synthetic route for fluorine-containing polycyclic indoles.

Key words： visible light catalysis; polycyclic indole; radical reaction; difluoroalkylation; cascade cyclization

参考文献

[1]
(a) Desmaele, D.; Jean, A. J. Org. Chem. 1994, 59, 2292.
[1]
(b) Jing, P.; Yang, Z.; Zhao, C. G.; Zheng, H. J.; Fang, B. W.; Xie, X. A.; She, X. G. Chem.-Eur. J. 2012, 18, 6729.
[1]
(c) Gartshore, C. J.; Lupton, D. W. Angew. Chem., Int. Ed. Engl. 2013, 52, 4113.
[1]
(d) Ni, D. S.; Wei, Y.; Ma, D. W. Angew. Chem., Int. Ed. 2018, 57, 10207.
[2]
(a) Yang, S. W.; Cordell, G. A. J. Nat. Prod. 1997, 60, 44.
[2]
(b) Knolker, H. J. Top. Curr. Chem. 2005, 2005, 115.
[3]
(a) Zhu, X. Y.; An, X. L.; Li, C. F.; Zhang, F. G.; Hua, Q. L.; Chen, J. R.; Xiao, W. J. ChemCatChem 2011, 3, 679.
[3]
(b) Park, S.; Ikehata, K.; Watabe, R.; Hidaka, Y.; Rajendran, A.; Sugiyama, H. Chem. Commun. 2012, 48, 10398.
[3]
(c) Petrova, G. P.; Ke, Z. F.; Park, S.; Sugiyama, H.; Morokuma, K. Chem. Phys. Lett. 2014, 600, 87.
[3]
(d) Park, S.; Zheng, L. J.; Kumakiri, S.; Sakashita, S.; Otomo, H.; Ikehata, K.; Sugiyama, H. ACS Catal. 2014, 4, 4070.
[4]
(a) Wang, M. Z.; Zhou, C. Y.; Che, C. M. Chem. Commun. 2011, 47, 1312.
[4]
(b) Wu, K. J.; Dai, L. X.; You, S. L. Org. Lett. 2012, 14, 3772.
[4]
(c) Wu, Q. F.; Zheng, C.; You, S. L. Angew. Chem., Int. Ed. 2012, 51, 1680.
[4]
(d) Kandukuri, S. R.; Jiao, L. Y.; Machotta, A. B.; Oestreich, M. Adv. Synth. Catal. 2014, 356, 1597.
[5]
(a) Gimeno, A.; Rodríguez-Gimeno, A.; Cuenca, A. B.; Arellano, C. R. D.; Medio-Simón, M.; Asensio, G. Chem. Commun. 2015, 51, 12384.
[5]
(b) Venning, A. R. O.; Bohan, P. T.; Alexanian, E. J. J. Am. Chem. Soc. 2015, 137, 3731.
[5]
(c) Kaldas, S. J.; Cannillo, A.; McCallum, T.; Barriault, L. Org. Lett. 2015, 17, 2864.
[5]
(d) Zhang, H. L.; Li, W. P.; Zhu, C. J. J. Org. Chem. 2017, 82, 2199.
[6]
Yao, X. T.; Shan, X. S.; Zu, L. S. Org. Lett. 2018, 20, 6498.
[7]
Bhattacherjee, D.; Ram, S.; Chauhan, A. S.; Yamini; Sheetal; Das, P. Chem.-Eur. J. 2019, 25, 5934.
[8]
Zhang, P. L.; Tsuji, N.; Ouyang, J.; List, B. J. Am. Chem. Soc. 2021, 143, 675.
[9]
Sun, W.; Raimbach, W. A. T.; Elliott, L. D.; Booker-Milburn, K. I.; Harrowven, D. C. Chem. Commun. 2022, 58, 383.
[10]
(a) Hu, J. B.; Zhang, W.; Wang, F. Chem. Commun. 2009, 7465.
[10]
(b) Fujiwara, Y.; Dixon, J. A.; Rodriguez, R. A.; Baxter, R. D.; Dixon, D. D.; Collins, M. R.; Blackmond, D. G.; Baran, P. S. J. Am. Chem. Soc. 2012, 134, 1494.
[10]
(c) An, L.; Xiao, Y. L.; Zhang, S.; Zhang, X. G. Angew. Chem., Int. Ed. 2018, 57, 6921.
[10]
(d) Gao, X.; Xiao, Y. L.; Wan, X. L.; Zhang, X. G. Angew. Chem., Int. Ed. 2018, 57, 3187.
[10]
(e) Li, C.; Cao, Y. X.; Wang, R.; Wang, Y. N.; Lan, Q.; Wang, X. S. Nat. Commun. 2018, 9, 4951.
[10]
(f) Huang, X.; Zhang, Y. G.; Zhang, C. S.; Zhang, L.; Xu, Y.; Kong, L. C.; Wang, Z. X.; Peng, B. Angew. Chem., Int. Ed. 2019, 58, 5956.
[10]
(g) Gao, Y.; Li, C. P.; Xu, B.; Liu, H. Org. Chem. Front. 2019, 6, 410.
[10]
(h) Jia, C. Q.; Wang, S. C.; Lv, X. L.; Li, G.; Zhong, L.; Zou, L.; Cui, X. L. Eur. J. Org. Chem. 2020, 2020, 1992.
[10]
(i) Zhang, Y.; Ge, J.; Luo, L.; Yan, S. Q.; Lai, G. W.; Mei, Z. Q.; Luo, H. Q.; Fan, X. L. Org. Lett. 2020, 22, 7952.
[10]
(j) Song, H.; Cheng, R.; Min, Q. Q.; Zhang, X. G. Org. Lett. 2020, 22, 7747.
[11]
(a) Zhang, B. S.; Gao, L. Y.; Zhang, Z.; Wen, Y. H.; Liang, Y. M. Chem. Commun. 2018, 54, 1185.
[11]
(b) Ma, X. X.; Mai, S. Y.; Zhou, Y.; Cheng, G. J.; Song, Q. L. Chem. Commun. 2018, 54, 8960.
[11]
(c) Li, C.; Cao, Y. X.; Jin, R. X.; Bian, K. J.; Qin, Z. Y.; Lan, Q.; Wang, X. S. Chem. Sci. 2019, 10, 9285.
[11]
(d) Zhou, Y. L.; Xiong, Z. M.; Qiu, J. Y.; Kong, L. C.; Zhu, G. G. Org. Chem. Front. 2019, 6, 1022.
[11]
(e) Zhang, R.; Zhang, Z. K.; Zhou, Q.; Yu, L. F.; Wang, J. B. Angew. Chem., Int. Ed. 2019, 58, 5744.
[11]
(f) Han, S. N.; Liu, S. D.; Liu, L.; Ackermann, L.; Li, J. Org. Lett. 2019, 21, 5387.
[11]
(g) Zhang, P. B.; Wang, C.; Cui, M. C.; Du, M. S.; Li, W. W.; Jia, Z. X.; Zhao, Q. Org. Lett. 2020, 22, 1149.
[12]
For review (a) Chen, Z. L.; Chen, J. R.; Xuan, J. Chin. Chem. Lett. 2022, 33, 2763.
[12]
(b) Xuan, J.; He, X. K.; Xiao, W. J. Chem. Soc. Rev. 2020, 49, 2546.
[12]
(c) Cai, B. G.; Xuan, J.; Xiao, W. J. Sci. Bull. 2019, 64, 337.
[13]
(a) Mei, H. B.; Liu, A. Y.; He, J. R.; Yu, Y. J.; Han, J. L. Org. Lett. 2022, 24, 2630.
[13]
(b) Mei, H. B.; Yu, Y. J.; Wang, C. T.; Liu, A. Y.; Han, J. L. Org. Chem. Front. 2022, 9, 2516.
[14]
(a) Huang, H. G.; Yu, M. L.; Su, X. L.; Guo, P.; Zhao, J.; Zhou, J. B.; Li, Y. J. Org. Chem. 2018, 83, 2425.
[14]
(b) Lin, S. N.; Chen, Y.; Luo, X. D.; Li, Y. Eur. J. Org. Chem. 2021, 2021, 4485.
[15]
Montalti, M.; Credi, A.; Prodi, L.; Gandolfi, M. T. Handbook of Photochemistry, 3rd ed., Boca Raton CRC/Taylor and Francis, Boca Raton, 2006, p. 83.
[16]
Teegardin, K.; Day, J. I.; Chan, J.; Weaver, J. Org. Process Res. Dev. 2016, 20, 1156.
[17]
Jung, J.; Kim, E.; You, Y.; Cho, E. J. Adv. Synth. Catal. 2014, 356, 2741.
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