Citation: Shengping Guo, Liyan Liu, Kangfei Hu, Qi Sun, Zhenggen Zha, Yu Yang, Zhiyong Wang. Electrochemical synthesis of 3-azido-indolines from amino-azidation of alkenes[J]. Chinese Chemical Letters, ;2021, 32(3): 1033-1036. doi: 10.1016/j.cclet.2020.09.041 shu

Electrochemical synthesis of 3-azido-indolines from amino-azidation of alkenes

Shengping Guo ^{a, 1} ,
Liyan Liu ^{a, 1} ,
Kangfei Hu ^a ,
Qi Sun ^a ,
Zhenggen Zha ^a ,
Yu Yang ^{b, *,} ,
Zhiyong Wang ^{a, *,}

a.
Hefei National Laboratory for Physical Sciences at Microscale, CAS Key Laboratory of Soft Matter Chemistry & Center for Excellence in Molecular Synthesis of Chinese Academy of Sciences, Collaborative Innovation Center of Suzhou Nano Science and Technology & School of Chemistry and Materials Science, University of Science and Technology of China, Hefei 230026, China
b.
School of Chemistry and Chemical Engineering, Hefei Normol University, Hefei 230601, China

yang529@hfnu.edu.cn

zwang3@ustc.edu.cn

Received Date: 17 August 2020
Revised Date: 11 September 2020
Accepted Date: 23 September 2020
Available Online: 27 October 2020

Figures(5)

An electrochemical amino-azidation of 2-aminostyrene with sodium azide (NaN₃) was developed, which can be carried out smoothly in water under metal-free condition, affording a series of 3-azido indolines with high yields.
- Electrochemical,
- Amino-azidation,
- 2-Aminostyrene,
- Metal-free,
- Oxidant-free,
- 3-Azido indolines
1. [1]
  D.M. Huryn, M. Okabe, Chem. Rev. 92 (1992) 1745-1768. doi: 10.1021/cr00016a004
2. [2]
  H. Li, R. Aneja, I. Chaiken, Molecules 18 (2013) 9797-9817. doi: 10.3390/molecules18089797
3. [3]
  D. Intrieri, P. Zardi, A. Caselli, E. Gallo, Chem. Commun. 50 (2014) 11440-11453. doi: 10.1039/C4CC03016H
4. [4]
  K. Banert, Synthesis 48 (2016) 2361-2375. doi: 10.1055/s-0035-1561454
5. [5]
  D. Huang, G. Yan, Adv. Synth. Catal. 359 (2017) 1600-1619. doi: 10.1002/adsc.201700103
6. [6]
  E. Scriven, K. Turnbull, Chem. Rev. 88 (1988) 297-368. doi: 10.1021/cr00084a001
7. [7]
  S. Brase, C. Gil, K. Knepper, V. Zimmermann, Angew. Chem. Int. Ed. 44 (2005) 5188-5240. doi: 10.1002/anie.200400657
8. [8]
  M. Minozzi, D. Nanni, P. Spagnolo, Chem. Eur. J. 15 (2009) 7830-7840. doi: 10.1002/chem.200802710
9. [9]
  J.L. Jat, M.P. Paudyal, H. Gao, et al., Science 343 (2014) 61-65. doi: 10.1126/science.1245727
10. [10]
  K. Guthikonda, P.M. Wehn, B.J. Caliando, J.D. Bois, Tetrahedron 62 (2006) 11331-11342. doi: 10.1016/j.tet.2006.07.099
11. [11]
  B. Wu, J.R. Parquette, T.V. RajanBabu, Science 326 (2009) 1662. doi: 10.1126/science.1180739
12. [12]
  H. Sun, C. Yang, R. Lin, W.J. Xia, Adv. Synth. Catal. 356 (2014) 2775-2780. doi: 10.1002/adsc.201400476
13. [13]
  S. Minakata, D. Kano, Y. Oderaotoshi, M. Komatsu, Angew. Chem. In. Ed. 43 (2004) 79-81. doi: 10.1002/anie.200352842
14. [14]
  S.N. Yu, Y.L. Li, J. Deng, Adv. Synth. Catal. 359 (2017) 1-11. doi: 10.1002/adsc.201601440
15. [15]
  H. Wang, M. Frings, C. Bolm, Org. Lett. 18 (2016) 2431-2434. doi: 10.1021/acs.orglett.6b00958
16. [16]
  M.T. Bovino, S.R. Chemler, Angew. Chem. Int. Ed 51 (2012) 3923-3927. doi: 10.1002/anie.201109044
17. [17]
  F.E. Michael, P.A. Sibbald, B.M. Cochran, Org. Lett. 10 (2008) 793-796. doi: 10.1021/ol702922c
18. [18]
  G.X. Ortiz, B. Kang, Q. Wang, J. Org. Chem. 79 (2014) 571-581. doi: 10.1021/jo4022666
19. [19]
  F.C. Sequeira, B.W. Turnpenny, S.R. Chemler, Angew. Chem. Int. Ed. 49 (2010) 6365-6368. doi: 10.1002/anie.201003499
20. [20]
  R. Francke, J. Beilstein, Org. Chem. 10 (2014) 2858-2873.
21. [21]
  S. Tang, X.L. Gao, A.W. Lei, Chem. Commun. 53 (2017) 3354-3356. doi: 10.1039/C7CC00410A
22. [22]
  L.J. Wesenberg, S. Herold, A. Shimizu, J.I. Yoshida, S.R. Waldvogel, Chem. Eur. J. 23 (2017) 12096-12099. doi: 10.1002/chem.201701979
23. [23]
  Z.W. Hou, Z.Y. Mao, H.C. Xu, Synlett 28 (2017) 1867-1872. doi: 10.1055/s-0036-1590842
24. [24]
  C.Y. Cai, H.C. Xu, Nat. Commun. 9 (2018) 3551-3557. doi: 10.1038/s41467-018-06020-8
25. [25]
  Z.W. Hou, Z.Y. Mao, Y.Y. Melcamu, X. Lu, H.C. Xu, Angew. Chem. Int. Ed. 57 (2018) 1636-1639. doi: 10.1002/anie.201711876
26. [26]
  X. Hu, G. Zhang, F. Bu, L. Nie, A.W. Lei, ACS Catal. 8 (2018) 9370-9375. doi: 10.1021/acscatal.8b02847
27. [27]
  Y.Y. Jiang, K. Xu, C.C. Zeng, Chem. Rev. 118 (2018) 4485-4540. doi: 10.1021/acs.chemrev.7b00271
28. [28]
  R. Mei, J. Koeller, L. Ackermann, Chem Commun. 54 (2018) 12879-12882. doi: 10.1039/C8CC07732K
29. [29]
  R. Mei, N. Sauermann, J.C.A. Oliveira, L. Ackermann, J. Am. Chem. Soc. 140 (2018) 7913-7921. doi: 10.1021/jacs.8b03521
30. [30]
  Y. Qiu, C. Tian, L. Massignan, T. Rogge, L. Ackermann, Angew. Chem. Int. Ed. 57 (2018) 5818-5822. doi: 10.1002/anie.201802748
31. [31]
  C. Tian, L. Massignan, T.H. Meyer, L. Ackermann, Angew. Chem. Int. Ed. 57 (2018) 2383-2387. doi: 10.1002/anie.201712647
32. [32]
  Z.H. Ye, M.R. Ding, Y.Q. Wu, et al., Green Chem. 20 (2018) 1732-1737. doi: 10.1039/C7GC03739B
33. [33]
  S. Zhang, L.J. Li, M.Y. Xue, et al., Org. Lett. 20 (2018) 3443-3446. doi: 10.1021/acs.orglett.8b00981
34. [34]
  X.L. Gao, P. Wang, Q.Q. Wang, J.T. Chen, A.W. Lei, Green Chem. 21 (2019) 4941-4945. doi: 10.1039/C9GC02118C
35. [35]
  J.W. Hua, Z. Fang, J. Xu, et al., Green Chem. 21 (2019) 4706-4711. doi: 10.1039/C9GC02131K
36. [36]
  Z.X. Ruan, Z.X. Huang, Z.N. Xu, et al., Org. Lett. 21 (2019) 1237-1240. doi: 10.1021/acs.orglett.9b00361
37. [37]
  J. Wu, Y.C. Dou, R. Guillot, C. Kouklovsky, G. Vincent, J. Am. Chem. Soc. 141 (2019) 2832-2837. doi: 10.1021/jacs.8b13371
38. [38]
  J.C. Siu, J.B. Parry, S. Lin, J. Am. Chem. Soc. 141 (2019) 2825-2831. doi: 10.1021/jacs.8b13192
39. [39]
  J.C. Siu, G.S. Sauer, A. Saha, et al., J. Am. Chem. Soc. 140 (2018) 12511-12520. doi: 10.1021/jacs.8b06744
40. [40]
  N. Fu, G.S. Sauer, A. Saha, A. Loo, S. Lin, Science 357 (2017) 575-579. doi: 10.1126/science.aan6206
41. [41]
  Y. Wang, L.L. Deng, H.B. Mei, et al., Green Chem. 20 (2018) 3444-3449. doi: 10.1039/C8GC01337C
42. [42]
  L.L. Zhang, G.T. Zhang, P. Wang, Y.L. Li, A.W. Lei, Org. Lett. 20 (2018) 7396-7399. doi: 10.1021/acs.orglett.8b03081
43. [43]
  L. Sun, Y. Yuan, M. Yao, et al., Org. Lett. 21 (2019) 1297-1300. doi: 10.1021/acs.orglett.8b03274
44. [44]
  G.S. Sauer, S. Lin, Adv. Synth. Catal. 8 (2018) 5175-5187.
45. [45]
  P. Xiong, H. Long, J.S. Song, et al., J. Am. Chem. Soc. 140 (2018) 16387-16391. doi: 10.1021/jacs.8b08592
46. [46]
  A. Jutand, Chem. Rev. 108 (2008) 2300-2347. doi: 10.1021/cr068072h
47. [47]
  J.I. Yoshida, K. Kataoka, R. Horcajada, A. Nagaki, Chem. Rev. 108 (2008) 2265-2299. doi: 10.1021/cr0680843
48. [48]
  R. Francke, R.D. Little, Chem. Soc. Rev. 43 (2014) 2492-2521. doi: 10.1039/c3cs60464k
49. [49]
  M. Yan, Y. Kawamata, P.S. Baran, Chem. Rev. 117 (2017) 13230-13319. doi: 10.1021/acs.chemrev.7b00397
50. [50]
  M.D. Karkas, Chem. Soc. Rev. 47 (2018) 5786-5865. doi: 10.1039/C7CS00619E
51. [51]
  C. Ma, P. Fang, T.S. Mei, Adv. Synth. Catal. 8 (2018) 7179-7189.
52. [52]
  N. Sauermann, T.H. Meyer, L. Ackermann, Chem. Eur. J. 24 (2018) 16209-16217. doi: 10.1002/chem.201802706
53. [53]
  N. Sauermann, T.H. Meyer, Y.A. Qiu, L. Ackermann, Adv. Synth. Catal. 8 (2018) 7086-7103.
54. [54]
  S.R. Waldvogel, S. Lips, M. Selt, B. Riehl, C.J. Kampf, Chem. Rev. 118 (2018) 6706-6765. doi: 10.1021/acs.chemrev.8b00233
55. [55]
  Q.L. Yang, P. Fang, T.S. Mei, Chin. J. Chem. 36 (2018) 338-352. doi: 10.1002/cjoc.201700740
56. [56]
  J.I. Yoshida, A. Shimizu, R. Hayashi, Chem. Rev. 118 (2018) 4702-4730. doi: 10.1021/acs.chemrev.7b00475
57. [57]
  T.H. Meyer, L.H. Finger, P. Gandeepan, L. Ackermann, Trends Analyt. Chem. 1 (2019) 63-76. doi: 10.1016/j.trechm.2019.01.011
58. [58]
  H.M. Wang, X.L. Gao, Z.C. Lv, T. Abdelilah, A.W. Lei, Chem. Rev. 119 (2019) 6769-6787. doi: 10.1021/acs.chemrev.9b00045
59. [59]
  E.J. Horn, B.R. Rosen, P.S. Baran, ACS Cent. Sci. 2 (2016) 302-308. doi: 10.1021/acscentsci.6b00091
60. [60]
  L.S. Kang, M.H. Luo, C.M. Lam, et al., Green Chem. 18 (2016) 3767-3774. doi: 10.1039/C6GC00666C
61. [61]
  P. Wang, S. Tang, A.W. Lei, Green Chem. 19 (2017) 2092-2095. doi: 10.1039/C7GC00468K
62. [62]
  P.F. Huang, P. Wang, S.C. Wang, S. Tang, A.W. Lei, Green Chem. 20 (2018) 4870-4874. doi: 10.1039/C8GC02463D
63. [63]
  K.D. Moeller, Chem. Rev. 118 (2018) 4817-4833. doi: 10.1021/acs.chemrev.7b00656
64. [64]
  S. Möhle, M. Zirbes, E. Rodrigo, et al., Angew. Chem. Int. Ed 57 (2018) 6018-6041. doi: 10.1002/anie.201712732
65. [65]
  S. Tang, Y.C. Liu, A.W. Lei, Chem 4 (2018) 27-45. doi: 10.1016/j.chempr.2017.10.001
66. [66]
  A. Wiebe, T. Gieshoff, S. Möhle, et al., Angew. Chem. Int. Ed. 57 (2018) 5594-5619. doi: 10.1002/anie.201711060
67. [67]
  M. Yan, Y. Kawamata, P.S. Baran, Angew. Chem. Int. Ed. 57 (2018) 4149-4155. doi: 10.1002/anie.201707584
68. [68]
  K.J. Li, Y.Y. Jiang, K. Xu, C.C. Zeng, B.G. Sun, Green Chem. 21 (2019) 4412-4421. doi: 10.1039/C9GC01474H
69. [69]
  Q.Y. Li, S.Y. Cheng, H.T. Tang, Y.M. Pan, Green Chem. 21 (2019) 5517-5520. doi: 10.1039/C9GC03028J
70. [70]
  Y.Z. Zhang, Z.Y. Mo, H.S. Wang, et al., Green Chem. 21 (2019) 3807-3811. doi: 10.1039/C9GC01201J
71. [71]
  J. Naud, C. Lemke, N. Goudreau, et al., Bioorg. Med. Chem. Lett. 18 (2008) 3400-3404. doi: 10.1016/j.bmcl.2008.04.012
72. [72]
  F. Wang, S.S. Stahl, Angew. Chem. Int. Ed. 58 (2019) 6385-6390. doi: 10.1002/anie.201813960
73. [73]
  K.F. Hu, Y. Zhang, Z.H. Zhou, et al., Org. Lett. 22 (2020) 5773-5777. doi: 10.1021/acs.orglett.0c01821
74. [74]
  X. Zong, Q.Z. Zheng, N. Jiao, Org. Biomol. Chem. 12 (2014) 1198-1202. doi: 10.1039/c3ob42118j
75. [75]
  S. Liang, C.C. Zeng, X.G. Luo, et al., Green Chem. 18 (2016) 2222-2230. doi: 10.1039/C5GC02626A
76. [76]
  I.S. El-Hallag, J. Chil, Chem. Soc. 55 (2010) 67-72.
77. [77]
  G.Q. Liu, Y.M. Li, J. Org. Chem. 79 (2014) 10094-10109. doi: 10.1021/jo501739j
1. [1]
  Tong Li , Leping Pan , Yan Zhang , Jihu Su , Kai Li , Kuiliang Li , Hu Chen , Qi Sun , Zhiyong Wang . Electrochemical construction of 2,5-diaryloxazoles via N–H and C(sp³)-H functionalization. Chinese Chemical Letters, 2024, 35(4): 108897-. doi: 10.1016/j.cclet.2023.108897
2. [2]
  Chunhua Ma , Mengjiao Liu , Siyu Ouyang , Zhenwei Cui , Jingjing Bi , Yuqin Jiang , Zhiguo Zhang . Metal-free construction of diverse 1,2,4-triazolo[1,5-a]pyridines on water. Chinese Chemical Letters, 2025, 36(1): 109755-. doi: 10.1016/j.cclet.2024.109755
3. [3]
  Chunxiu Yu , Zelin Wu , Hongle Shi , Lingyun Gu , Kexin Chen , Chuan-Shu He , Yang Liu , Heng Zhang , Peng Zhou , Zhaokun Xiong , Bo Lai . Insights into the electron transfer mechanisms of peroxydisulfate activation by modified metal-free acetylene black for degradation of sulfisoxazole. Chinese Chemical Letters, 2024, 35(8): 109334-. doi: 10.1016/j.cclet.2023.109334
4. [4]
  Tao Zhou , Jing Zhou , Yunyun Liu , Jie-Ping Wan , Fen-Er Chen . Transition metal-free tunable synthesis of 3-(trifluoromethylthio) and 3-trifluoromethylsulfinyl chromones via domino C–H functionalization and chromone annulation of enaminones. Chinese Chemical Letters, 2024, 35(11): 109683-. doi: 10.1016/j.cclet.2024.109683
5. [5]
  Xiaodan Wang , Yingnan Liu , Zhibin Liu , Zhongjian Li , Tao Zhang , Yi Cheng , Lecheng Lei , Bin Yang , Yang Hou . Highly efficient electrosynthesis of H₂O₂ in acidic electrolyte on metal-free heteroatoms co-doped carbon nanosheets and simultaneously promoting Fenton process. Chinese Chemical Letters, 2024, 35(7): 108926-. doi: 10.1016/j.cclet.2023.108926
6. [6]
  Lang Gao , Cen Zhou , Rui Wang , Feng Lan , Bohang An , Xiaozhou Huang , Xiao Zhang . Unveiling inverse vulcanized polymers as metal-free, visible-light-driven photocatalysts for cross-coupling reactions. Chinese Chemical Letters, 2024, 35(4): 108832-. doi: 10.1016/j.cclet.2023.108832
7. [7]
  Xiuwen Xu , Quan Zhou , Yacong Wang , Yunjie He , Qiang Wang , Yuan Wang , Bing Chen . Expanding the toolbox of metal-free organic halide perovskite for X-ray detection. Chinese Chemical Letters, 2024, 35(9): 109272-. doi: 10.1016/j.cclet.2023.109272
8. [8]
  Kexin Yin , Jingren Yang , Yanwei Li , Qian Li , Xing Xu . Metal-free diatomaceous carbon-based catalyst for ultrafast and anti-interference Fenton-like oxidation. Chinese Chemical Letters, 2024, 35(12): 109847-. doi: 10.1016/j.cclet.2024.109847
9. [9]
  Hai-Yang Song , Jun Jiang , Yu-Hang Song , Min-Hang Zhou , Chao Wu , Xiang Chen , Wei-Min He . Supporting-electrolyte-free electrochemical [2 + 2 + 1] annulation of benzo[d]isothiazole 1,1-dioxides, N-arylglycines and paraformaldehyde. Chinese Chemical Letters, 2024, 35(6): 109246-. doi: 10.1016/j.cclet.2023.109246
10. [10]
  Jianhui Yin , Wenjing Huang , Changyong Guo , Chao Liu , Fei Gao , Honggang Hu . Tryptophan-specific peptide modification through metal-free photoinduced N-H alkylation employing N-aryl glycines. Chinese Chemical Letters, 2024, 35(6): 109244-. doi: 10.1016/j.cclet.2023.109244
11. [11]
  Guoju Guo , Xufeng Li , Jie Ma , Yongjia Shi , Jian Lv , Daoshan Yang . Photocatalyst/metal-free sequential C–N/C–S bond formation: Synthesis of S-arylisothioureas via photoinduced EDA complex activation. Chinese Chemical Letters, 2024, 35(11): 110024-. doi: 10.1016/j.cclet.2024.110024
12. [12]
  Ruixin Liu , Feng Shi , Yanping Xia , Haibing Zhu , Jiawen Cao , Kai Peng , Chuanli Ren , Juan Li , Zhanjun Yang . Universal MOF nanozyme-induced catalytic amplification strategy for label-free electrochemical immunoassay. Chinese Chemical Letters, 2024, 35(11): 109664-. doi: 10.1016/j.cclet.2024.109664
13. [13]
  Xueyang Zhao , Bangwei Deng , Hongtao Xie , Yizhao Li , Qingqing Ye , Fan Dong . Recent process in developing advanced heterogeneous diatomic-site metal catalysts for electrochemical CO₂ reduction. Chinese Chemical Letters, 2024, 35(7): 109139-. doi: 10.1016/j.cclet.2023.109139
14. [14]
  Tinghui Yang , Min Kuang , Jianping Yang . Mesoporous CuCe dual-metal catalysts for efficient electrochemical reduction of CO2 to methane. Chinese Journal of Structural Chemistry, 2024, 43(8): 100350-100350. doi: 10.1016/j.cjsc.2024.100350
15. [15]
  Jie Li , Huida Qian , Deyang Pan , Wenjing Wang , Daliang Zhu , Zhongxue Fang . Efficient Synthesis of Anethaldehyde Induced by Visible Light. University Chemistry, 2024, 39(4): 343-350. doi: 10.3866/PKU.DXHX202310076
16. [16]
  Haiying Lu , Weijie Li . The electrolyte solvation and interfacial chemistry for anode-free sodium metal batteries. Chinese Journal of Structural Chemistry, 2024, 43(11): 100334-100334. doi: 10.1016/j.cjsc.2024.100334
17. [17]
  Fei Yin , Erli Yang , Xue Ge , Qian Sun , Fan Mo , Guoqiu Wu , Yanfei Shen . Coupling WO₃₋_x dots-encapsulated metal-organic frameworks and template-free branched polymerization for dual signal-amplified electrochemiluminescence biosensing. Chinese Chemical Letters, 2024, 35(4): 108753-. doi: 10.1016/j.cclet.2023.108753
18. [18]
  Muhammad Humayun , Mohamed Bououdina , Abbas Khan , Sajjad Ali , Chundong Wang . Designing single atom catalysts for exceptional electrochemical CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(1): 100193-100193. doi: 10.1016/j.cjsc.2024.100193
19. [19]
  Boqiang Wang , Yongzhuo Xu , Jiajia Wang , Muyang Yang , Guo-Jun Deng , Wen Shao . Transition-metal free trifluoromethylimination of alkenes enabled by direct activation of N-unprotected ketimines. Chinese Chemical Letters, 2024, 35(9): 109502-. doi: 10.1016/j.cclet.2024.109502
20. [20]
  Xinxiu Yan , Xizhe Huang , Yangyang Liu , Weishang Jia , Hualin Chen , Qi Yao , Tao Chen . Hyperbranched polyamidoamine protective layer with phosphate and carboxyl groups for dendrite-free Zn metal anodes. Chinese Chemical Letters, 2024, 35(10): 109426-. doi: 10.1016/j.cclet.2023.109426

Get Citation

PDF

XML

Metrics

PDF Downloads(7)
Abstract views(1047)
HTML views(155)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142