ARTICLES

Electrochemical Annulations of o-Alkynylanilines for Synthesis of 3-Iodoindoles

  • Hehua Xu ,
  • Xiangtai Meng ,
  • Yu Zheng ,
  • Jinyue Luo ,
  • Shenlin Huang
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  • a Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037
    b International Innovation Center for Forest Chemicals and Materials, Nanjing 210037
* Corresponding authors. E-mail: ;

Received date: 2021-12-08

  Revised date: 2021-12-19

  Online published: 2021-12-22

Supported by

National Natural Science Foundation of China(32171724)

Abstract

Indole, as one of the most important nitrogen-containing heterocyclic compound, is found widely in various natural products and synthetic drugs. 3-Iodoindoles play an important role as intermediate in the selective functionalization of indoles. 3-iodoindoles could be conveniently synthesized by electrochemical annulations of o-alkynylanilines with readily available iodide salt. This sustainable electrolysis strategy provides an efficient access to a series of 3-iodoindoles in good to excellent yields under external oxidant-free, base-free conditions and features broad functional group tolerance.

Cite this article

Hehua Xu , Xiangtai Meng , Yu Zheng , Jinyue Luo , Shenlin Huang . Electrochemical Annulations of o-Alkynylanilines for Synthesis of 3-Iodoindoles[J]. Chinese Journal of Organic Chemistry, 2021 , 41(12) : 4696 -4703 . DOI: 10.6023/cjoc202112016

References

[1]
(a) Sravanthi, T. V.; Manju, S. L. Eur. J. Pharm. Sci. 2016, 91, 1.
[1]
(b) Holman, K. R.; Stanko, A. M.; Reisman, S. E. Chem. Soc. Rev. 2021, 50, 7891.
[1]
(c) Kochanowska-Karamyan, A. J.; Hamann, M. T. Chem. Rev. 2010, 110, 4489.
[1]
(d) Yu, R.; Fang, X. Chin. J. Org. Chem. 2021, 41, 2532. (in Chinese)
[1]
( 余融融, 方显杰, 有机化学, 2021, 41, 2532.)
[1]
(e) Wang, R.; Xu, L.; Lu, Y.; Jiang, B.; Hao, W. Chin. J. Org. Chem. 2021, 41, 1582. (in Chinese)
[1]
( 王榕, 徐立晨, 卢逸, 姜波, 郝文娟, 有机化学, 2021, 41, 1582.)
[1]
(f) Gao, Z.; Wang, Y.; Song, H.; Xu, Z.; Jia, Y. Chin. J. Org. Chem. 2021, 41, 3126. (in Chinese)
[1]
( 高中润, 王媛, 宋航, 徐正仁, 贾彦兴, 有机化学, 2021, 41, 3126.)
[1]
(g) Li, P.; Zhou, Z.; Yang, F.; Xu, Y.; Zhang, X. Chin. J. Org. Chem. 2021, 41, 3235. (in Chinese)
[1]
( 李萍, 周志强, 杨帆, 徐瑶, 张小祥, 有机化学, 2021, 41, 3235.)
[2]
(a) Yue, D.; Larock, R. C. Org. Lett. 2004, 6, 1037.
[2]
(b) Zhang, C.-P.; Wang, Z.-L.; Chen, Q.-Y.; Zhang, C.-T.; Gu, Y.-C.; Xiao, J.-C. Angew. Chem. Int. Ed. 2011, 50, 1896.
[2]
(c) Al-Saedy, M. A. E.; Harrity, J. P. A. Synlett. 2016, 27, 1674.
[2]
(d) Chintawar, C. C.; Yadav, A. K.; Patil, N. T. Angew. Chem. Int. Ed. 2020, 59, 11808.
[2]
(e) Campo, M. A.; Larock, R. C. J. Org. Chem. 2002, 67, 5616.
[3]
(a) Barluenga, J.; Trincado, M.; Rubio, E.; González, J. M. Angew. Chem. Int. Ed. 2003, 42, 2406.
[3]
(b) Amjad, M.; Knight, D. W. Tetrahedron Lett. 2004, 45, 539.
[3]
(c) Li, Y.-L.; Li, J.; Yu, S.-N.; Wang, J.-B.; Yu, Y.-M.; Deng, J. Tetrahedron 2015, 71, 8271.
[4]
(a) Novaes, L. F. T.; Liu, J.; Shen, Y.; Lu, L.; Meinhardt, J. M.; Lin, S. Chem. Soc. Rev. 2021, 50, 7941.
[4]
(b) Liu, J.; Lu, L.; Wood, D.; Lin, S. ACS Cent. Sci. 2020, 6, 1317.
[4]
(c) Pollok, D.; Waldvogel, S. R. Chem. Sci. 2020, 11, 12386.
[4]
(d) Little, R. D. J. Org. Chem. 2020, 85, 13375.
[4]
(e) Kingston, C.; Palkowitz, M. D.; Takahira, Y.; Vantourout, J. C.; Peters, B. K.; Kawamata, Y.; Baran, P. S. Acc. Chem. Res. 2020, 53, 72.
[4]
(f) Wang, X.; Xu, X.; Wang, Z.; Fang, P.; Mei, T. Chin. J. Org. Chem. 2020, 40, 3738. (in Chinese)
[4]
( 王向阳, 徐学涛, 王振华, 方萍, 梅天胜, 有机化学, 2020, 40, 3738.)
[4]
(g) Xiong, P.; Xu, H.-C. Acc. Chem. Res. 2019, 52, 3339.
[4]
(h) Yuan, Y.; Lei, A. Acc. Chem. Res. 2019, 52, 3309.
[4]
(i) Wiebe, A.; Gieshoff, T.; Möhle, S.; Rodrigo, E.; Zirbes, M.; Waldvogel, S. R. Angew. Chem. Int. Ed. 2018, 57, 5594.
[4]
(j) Yan, M.; Kawamata, Y.; Baran, P. S. Chem. Rev. 2017, 117, 13230.
[4]
(k) Francke, R.; Little, R. D. Chem. Soc. Rev. 2014, 43, 2492.
[4]
(l) Kingston, C.; Palkowitz, M. D.; Takahira, Y.; Vantourout, J. C.; Peters, B. K.; Kawamata, Y.; Baran, P. S. Acc. Chem. Res. 2020, 53, 72.
[4]
(m) Huang, C.; Li, Z.-Y.; Song, J.; Xu, H.-C. Angew. Chem. Int. Ed. 2021, 60, 11237.
[4]
(n) Kai, S.; Xiao, F.; Yu, B.; He, W.-M. Chin. J. Catal. 2021, 42, 1921.
[4]
(o) Liu, F.; Dai, J.; Cheng, X. Chin. J. Org. Chem. 2021, 41, 4014. (in Chinese)
[4]
( 刘峰, 戴洁, 程旭, 有机化学, 2021, 41, 4014.)
[4]
(p) Jiang, J.; Wang, Z.; He, W.-M. Chin. Chem. Lett. 2021, 32, 1591.
[4]
(q) Li, M.; Wang, R.; Hao, W.; Jiang, B. Chin. J. Org. Chem. 2020, 40, 1540. (in Chinese)
[4]
( 李梦帆, 王榕, 郝文娟, 姜波, 有机化学, 2020, 40, 1540.)
[4]
(r) Chen, J.-Y.; Lin, Y.-W.; He, W.-M. Chin. Chem. Lett. 2020, 31, 2989.
[4]
(s) Gao, J.; Weng, X.; Ma, C.; Xu, X.; Fang, P.; Mei, T. Chin. J. Org. Chem. 2021, 41, 3223. (in Chinese)
[4]
( 高君青, 翁信军, 马聪, 徐学涛, 方萍, 梅天胜, 有机化学, 2021, 41, 3223.)
[4]
(t) Meng, W.; Xu, K.; Guo, B.; Zeng, C. Chin. J. Org. Chem. 2021, 41, 2621. (in Chinese)
[4]
( 孟薇, 徐坤, 郭兵兵, 曾程初, 有机化学, 2021, 41, 2621.)
[4]
(u) Meng, Z.; Feng, C.; Xu, K. Chin. J. Org. Chem. 2021, 41, 2535. (in Chinese)
[4]
( 蒙泽银, 冯承涛, 徐坤, 有机化学, 2021, 41, 2535.)
[4]
(v) Zhou, Y.; Zhao, Z.; Zeng, L.; Li, M.; He, Y.; Gu, L. Chin. J. Org. Chem. 2021, 41, 1072. (in Chinese)
[4]
( 周娅琴, 赵志恒, 曾亮, 李鸣, 何永辉, 谷利军, 有机化学, 2021, 41, 1072.)
[4]
(w) Wang, N.; Xu, J.; Mei, H.; Moriwaki, H.; Izawa, K.; Soloshonol, V.; Han, J. Chin. J. Org. Chem. 2021, 41, 3034. (in Chinese)
[4]
( 王娜娜, 徐敬成, 梅海波, Hiroki Moriwaki, Kunisuke Izawa, Vadim A. Soloshonok, 韩建林, 有机化学, 2021, 41, 3034.)
[5]
(a) Wang, B.; Liu, Z.; Tong, Z.; Gao, B.; Ding, H. Angew. Chem. Int. Ed. 2021, 60, 148926.
[5]
(b) Wu, Y; Chen, J.-Y.; Ning, J.; Jiang, X.; Deng, J.; Deng, Y.; Xu, R.; He, W.-M. Green Chem. 2021, 23, 3950.
[5]
(c) Kai, S.; Xiao, F.; Yu, B.; He, W.-M. Chin. J. Catal. 2021, 42, 1921.
[5]
(d) Chen, J.-Y.; Wu, H.-Y.; Gui, Q.-W.; Yan, S.-S.; Deng, J.; Lin, Y.-W.; Cao, Z. He, W.-M. Chin. J. Catal. 2021, 42, 1445.
[5]
(e) Wu, Z.-L.; Chen, J.-Y.; Tian, X.-Z.; Ouyang, W.-T.; Zhang, Z.-T.; He, W.-M. Chin. Chem. Lett. 2021, DOI: 10.1016/j.cclet.2021.08.071.
[5]
(f) Chen, J.-Y.; Zhong, C.-T.; Gui, Q.-W.; Zhou, Y.-M.; Fang, Y.-Y.; Liu, K.-J.; Lin, Y.-W.; Cao, Z.; He, W.-M. Chin. Chem. Lett. 2021, 32, 475.
[5]
(g) Yi, R.-N.; Wu, Z.-L.; Ouyang, W.-T.; Wang, W.-F.; He, W.-M. Tetrahedron Lett. 2021, 77, 153257.
[5]
(h) Chen, J.-Y.; Wu, H.-Y.; Gui, Q.-W.; Han, X.-R.; Wu, Y.; Du, K.; Cao, Z.; Lin, Y.-W.; He, W.-M. Org. Lett. 2020, 22, 2206.
[5]
(i) Xiong, Y.; Zhang, J.; Shen, Q.; Huang, J.; Wang, T. Chin. J. Org. Chem. 2021, 41, 2735. (in Chinese)
[5]
( 熊云奎, 张健叶, 申裙, 黄嘉宇, 王涛, 有机化学, 2021, 41, 2735.)
[5]
(j) Ma, H.; Mei, T. Chin. J. Org. Chem. 2020, 40, 3982. (in Chinese)
[5]
( 马红星, 梅天胜, 有机化学, 2020, 40, 3982.)
[5]
(k) Jiang, Y.-Y.; Zeng, C.-C. Chin. J. Org. Chem. 2020, 40, 2999. (in Chinese)
[5]
( 蒋洋叶, 曾程初, 有机化学, 2020, 40, 2999.)
[5]
(l) Ye, Z.; Zhang, F. Chin. J. Org. Chem. 2020, 40, 241. (in Chinese)
[5]
( 叶增辉, 张逢质, 有机化学, 2020, 40, 241.)
[5]
(m) Feng, E.; Hou, Z.; Xu, H. Chin. J. Org. Chem. 2019, 39, 1424. (in Chinese)
[5]
( 冯恩祺, 侯中伟, 徐海超, 有机化学, 2019, 39, 1424.)
[6]
Yuan, Y.; Lei, A. Nat. Commun. 2020, 11, 802.
[7]
Liu, K.; Song, C.; Lei, A. Org. Biomol. Chem. 2018, 16, 2375.
[8]
Zhang, J.; Shi, S.-Q.; Hao, W.-J.; Dong, G.-Y.; Tu, S.-J.; Jiang, B. J. Org. Chem. 2021, 86, 15886.
[9]
Meng, X.; Xu, H.; Cao, X.; Cai, X.; Luo, J.; Wang, F.; Huang, S. Org. Lett. 2020, 22, 6827.
[10]
Li, J.-H.; Qin, J.-H.; Luo, M.-J.; An, D.-L. Angew. Chem. Int. Ed. 2020, 60, 1861.
[11]
(a) Wang, F.; Stahl, S. S. Angew. Chem. Int. Ed. 2019, 58, 6385.
[11]
(b) Mo, Z.-Y.; Swaroop, T. R.; Tong, W.; Zhang, Y.-Z.; Tang, H.-T.; Pan, Y.-M.; Sun, H.-B.; Chen, Z.-F. Green Chem. 2018, 20, 4428.
[11]
(c) Scheide, M. R.; Nicoleti, C. R.; Martins, G. M.; Braga, A. L. Org. Biomol. Chem. 2021, 19, 2578.
[12]
(a) Zhang, T.-S.; Hao, W.-J.; Wang, R.; Wang, S.-C.; Tu, S.-J.; Jiang, B. Green Chem. 2020, 22, 4259.
[12]
(b) Zuo, H.-D.; Hao, W.-J.; Zhu, C.-F.; Guo, C.; Tu, S.-J.; Jiang, B. Org. Lett. 2020, 22, 4471.
[13]
(a) Aggarwal, T.; Kumar, S.; Verma, A. K. Org. Biomol. Chem. 2016, 14, 7639.
[13]
(b) Liang, S.; Zeng, C.-C.; Luo, X.-G.; Ren, F.-Z.; Tian, H.-Y.; Sun, B.-G.; Little, R. D. Green Chem. 2016, 18, 2222.
[13]
(c) Midorikawa, K.; Suga, S.; Yoshida, J. Chem. Commun. 2006, 3794.
[14]
Yin, Y.; Ma, W.; Chai, Z.; Zhao, G. J. Org. Chem. 2007, 72, 5731.
[15]
(a) Voth, C. N.; Dake, G. R. Eur. J. Org. Chem. 2020, 2020, 744.
[15]
(b) Abe, M.; Jean, A.; Blanchet, J.; Rouden, J.; Maddaluno, J.; Paolis, M. D. J. Org. Chem. 2019, 84, 15448.
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