Citation: Chunngai Hui, Shiping Wang, Chunfa Xu. Dinitrogen extrusion from diazene in organic synthesis[J]. Chinese Chemical Letters, ;2022, 33(8): 3695-3700. doi: 10.1016/j.cclet.2022.03.073 shu

Dinitrogen extrusion from diazene in organic synthesis

Chunngai Hui ^{a, c} ,
Shiping Wang ^{b, *,} ,
Chunfa Xu ^{a, *,}

a.
Institute of Pharmaceutical Science and Technology, College of Chemistry, Fuzhou University, Fuzhou 350108, China
b.
National Engineering Research Center of Chemical Fertilizer Catalyst, College of Chemical Engineering, Fuzhou University, Fuzhou 350108, China
c.
Max Planck Institute of Molecular Physiology, Department of Chemical Biology, Dortmund 44227, Germany

wangsp@fzu.edu.cn

xucf@fzu.edu.cn

Received Date: 7 January 2022
Revised Date: 15 March 2022
Accepted Date: 17 March 2022
Available Online: 19 March 2022

Figures(6)

Radical-mediated reactions have many advantages in the construction of complex molecular scaffolds by forging chemical bonds of high challenge. Diazenes, including 1, 1-diazenes and 1, 2-diazenes, can generate biradical species via nitrogen extrusion under thermal or photochemical conditions. The superior reactivity of the generated biradical enables various types of synthetic transformations with excellent chemoselectivity and has been applied to the complex natural products synthesis. In this mini-review, the modes of reaction are summarized and discussed, namely ring contraction via nitrogen deletion, homo or heterodimerization, trimethylenemethane (TMM)-diyl cycloaddition. Applications of these classes of reactions in complex natural product synthesis are illustrated. Last but not least, the current state, future directions, and opportunities for dinitrogen extrusion reaction from diazenes are highlighted and discussed.
- Diazene,
- Biradical,
- Dimerization,
- Ring contraction,
- Natural product synthesis
1. [1]
  K.R. Campos, P.J. Coleman, J.C. Alvarez, et al., Science 363 (2019) eaat0805. doi: 10.1126/science.aat0805
2. [2]
  G.M. Whitesides, Angew. Chem. Int. Ed. 54 (2015) 3196-3209. doi: 10.1002/anie.201410884
3. [3]
  X. Jiang, L. Shi, H. Liu, A.H. Khan, J.S. Chen, Org. Biomol. Chem. 10 (2012) 8383-8392. doi: 10.1039/c2ob26152a
4. [4]
  H.Y. Lee, Acc. Chem. Res. 48 (2015) 2308-2319. doi: 10.1021/acs.accounts.5b00178
5. [5]
  J. Kim, M. Movassaghi, Acc. Chem. Res. 48 (2015) 1159-1171. doi: 10.1021/ar500454v
6. [6]
  P.S. Engel, Chem. Rev. 80 (1980) 99-150. doi: 10.1021/cr60324a001
7. [7]
  Y. Ren, S. Zhu, Q. Zhou, Org. Biomol. Chem. 16 (2018) 3087-3094. doi: 10.1039/c8ob00473k
8. [8]
  B.D. Bergstrom, L.A. Nickersom, J.T. Shaw, L.W. Souza, Angew. Chem. Int. Ed. 60 (2021) 6864-6878. doi: 10.1002/anie.202007001
9. [9]
  H.M.L. Davies, R.E.J. Beckwith, Chem. Rev. 103 (2003) 2861-2904.
10. [10]
  L. Dubinsky, B.P. Krom, M.M. Meijler, Bioorg. Med. Chem. 20 (2012) 554-570.
11. [11]
  M.P. Doyle, J. Tauton, S. Oon, et al., Tetrahedron Lett. 29 (1988) 5863-5866. doi: 10.1016/S0040-4039(00)82210-8
12. [12]
  C. Xu, V.U.B. Rao, F. Chen, Green. Synth. Catal. 3 (2022) 1-3. doi: 10.1016/j.gresc.2021.12.001
13. [13]
  C. Zippel, J. Seibert, S. Bräse, Angew. Chem. Int. Ed. 60 (2021) 19522-19524. doi: 10.1002/anie.202107490
14. [14]
  Z. Wang, J. Liu, Beilstein J. Org. Chem. 16 (2020) 3015–3031. doi: 10.3762/bjoc.16.251
15. [15]
  G. Koga, J.C. Warner, J.P. Anselme, Radical reactions of azo, hydrazo and azoxy compounds, in: S. Patai, (Eds. ), The Chemistry of the Hydrazo, Azo and Azoxy Groups. John Wiley & Sons, 1997.
16. [16]
  J. Liu, Y. Yang, K. Ouyang, W. Zhang, Green Synth. Catal. 2 (2021) 87-122. doi: 10.1117/12.2604794
17. [17]
  H. Yi, G. Zhang, H. Wang, et al., Chem. Rev. 117 (2017) 9016-9085. doi: 10.1021/acs.chemrev.6b00620
18. [18]
  Y. Fan, X. Gao, J. Yue, Sci. China Chem. 59 (2016) 1126-1141. doi: 10.1007/s11426-016-0233-1
19. [19]
  B. Zhen, X. Suo, J. Dang, et al., Chin. Chem. Lett. 32 (2021) 2338-2341.
20. [20]
  Z. Meng, F. Mi, F. Lu, et al., Chin. Chem. Lett. 31 (2020) 1903-1905.
21. [21]
  J. Li, K. Gao, M. Bian, H. Ding, Org. Chem. Front. 7 (2020) 136-154.
22. [22]
  S. Poplata, A. Tröster, Y. Zou, T. Bach, Chem. Rev. 116 (2016) 9748-9815. doi: 10.1021/acs.chemrev.5b00723
23. [23]
  Y. Xu, M.L. Conner, M.K. Brown, Angew. Chem. Int. Ed. 54 (2015) 11918-11928. doi: 10.1002/anie.201502815
24. [24]
  E.N. Hancock, J.M. Wahl, M.K. Brown, Nat. Prod. Rep. 36 (2019) 1383-1393. doi: 10.1039/c8np00083b
25. [25]
  C. Ebner, E.M. Carreira, Chem. Rev. 117 (2017) 11651-11679. doi: 10.1021/acs.chemrev.6b00798
26. [26]
  M. Mato, A. Franchino, C. García-Morales, A.M. Echavarren, Chem. Rev. 121 (2021) 8613-8684. doi: 10.1021/acs.chemrev.0c00697
27. [27]
  A. Padwa, A. Rodriguez, Tetrahedron Lett. 22 (1981) 187-190.
28. [28]
  M.S. Kirillova, M.E. Muratore, R. Dorel, A.M. Echavarren, J. Am. Chem. Soc. 138 (2016) 3671-3674. doi: 10.1021/jacs.6b01428
29. [29]
  P.A. Wender, J.M. Kee, J.M. Warrington, Science 320 (2008) 649-652. doi: 10.1126/science.1154690
30. [30]
  V. Mascitti, E.J. Corey, J. Am. Chem. Soc. 126 (2004) 15664-15665. doi: 10.1021/ja044089a
31. [31]
  M. Movassaghi, O.K. Ahmad, S.P. Lathrop, J. Am. Chem. Soc. 133 (2011) 13002-13005. doi: 10.1021/ja2057852
32. [32]
  S. P Lathrop, M. Pompeo, W.T.T. Chang, M. Movassaghi, J. Am. Chem. Soc. 138 (2016) 7763-7769. doi: 10.1021/jacs.6b04072
33. [33]
  M.M. Pompeo, J.H. Cheah, M. Movassaghi, J. Am. Chem. Soc. 141 (2019) 14411-14420. doi: 10.1021/jacs.9b07397
34. [34]
  P. Lindovska, M. Movassaghi, J. Am. Chem. Soc. 139 (2017) 17590-17596. doi: 10.1021/jacs.7b09929
35. [35]
  B.M. Trost, Angew. Chem. Int. Ed. 25 (1986) 1-20.
36. [36]
  J.A. Berson, C.D. Duncan, L.R. Corwin, J. Am. Chem. Soc. 96 (1974) 6175-6177. doi: 10.1021/ja00826a035
37. [37]
  R.D. Little, G.W. Muller, J. Am. Chem. Soc. 101 (1979) 7129-7130. doi: 10.1021/ja00517a086
38. [38]
  R.D. Little, G.W. Muller, J. Am. Chem. Soc. 103 (1981) 2744-2749. doi: 10.1021/ja00400a043
39. [39]
  T. Kang, W.Y. Kim, Y. Yoon, B. G. Kim, H.Y. Lee, J. Am. Chem. Soc. 133 (2011) 18050-18053. doi: 10.1021/ja207591e
40. [40]
  T. Kang, S.B. Song, W.Y. Kim, B.G. Kim, H.Y. Lee, J. Am. Chem. Soc. 136 (2014) 10274-10276. doi: 10.1021/ja5054412
41. [41]
  H. Lee, T. Kang, H.Y. Lee, Angew. Chem. Int. Ed. 56 (2017) 8254-8257. doi: 10.1002/anie.201704492
42. [42]
  W.D. Hinsberg III, P.B. Dervan, J. Am. Chem. Soc. 100 (1978) 1608-1610. doi: 10.1021/ja00473a051
43. [43]
  P.G. Schultz, P.B. Dervan, J. Am. Chem. Soc. 102 (1980) 878-880. doi: 10.1021/ja00522a090
44. [44]
  P.G. Schultz, P.B. Dervan, J. Am. Chem. Soc. 103 (1981) 1563-1564. doi: 10.1021/ja00396a048
45. [45]
  P.G. Schultz, P.B. Dervan, J. Am. Chem. Soc. 104 (1982) 6660-6668. doi: 10.1021/ja00388a031
46. [46]
  S.H. Kennedy, B.D. Dherange, K.J. Berger, M.D. Levin, Nature 593 (2021) 223-227. doi: 10.1038/s41586-021-03448-9
47. [47]
  H, Qin, W. Cai, S. Wang, et al. Angew. Chem. Int. Ed. 60 (2021) 20678-20683.
48. [48]
  X. Zou, J. Zou, L. Yang, G. Li, H. Lu, J. Org. Chem. 82 (2017) 4677-4688. doi: 10.1021/acs.joc.7b00308
49. [49]
  C. Hui, L. Brieger, C. Strohmann, A.P. Antonchick, J. Am. Chem. Soc. 143 (2021) 18864-18870. doi: 10.1021/jacs.1c10175
50. [50]
  L.G. O'Neil, J.F. Bower, Angew. Chem. Int. Ed. 60 (2020) 25640-25666.
51. [51]
  M. Zenzola, R. Doran, L. Degennaro, R. Luisi, J.A. Bull, Angew. Chem. Int. Ed. 55 (2016) 7203-7207. doi: 10.1002/anie.201602320
52. [52]
  T. Glachet, H. Marzag, N.S. Rosa, et al. J. Am. Chem. Soc. 141 (2019) 13689-13696. doi: 10.1021/jacs.9b07035
53. [53]
  B.D. Dherange, P.Q. Kelly, J.P. Liles, M.S. Sigman, M.D. Levin, J. Am. Chem. Soc. 143 (2021) 11337-11344. doi: 10.1021/jacs.1c06287
54. [54]
  D. Ma, B.S. Martin, K.S. Gallagher, T. Saito, M. Dai, J. Am. Chem. Soc. 143 (2021) 16383-16387. doi: 10.1021/jacs.1c08626
55. [55]
  A.M. Szpilman, E.M. Carreira, Angew. Chem. Int. Ed., 49 (2010) 9592-9628. doi: 10.1002/anie.200904761
56. [56]
  W. Adam, T. Oppenländer, Can. J. Chem. 63 (1985) 1829-1832. doi: 10.1139/v85-303
57. [57]
  A.K. Clarke, W.P. Unsworth, Chem. Sci. 11 (2020) 2876-2881. doi: 10.1039/d0sc00568a
58. [58]
  M.D.E. Forbes, Carbon-Centered Free Radicals and Radical Cations: Structure, Reactivity, and Dynamics, John Wiley & Sons, 2009.
1. [1]
  Peng Chen , Lijuan Liang , Yufei Zhu , Zhimin Xing , Zhenhua Jia , Teck-Peng Loh . Strategies for constructing seven-membered rings: Applications in natural product synthesis. Chinese Chemical Letters, 2024, 35(6): 109229-. doi: 10.1016/j.cclet.2023.109229
2. [2]
  Wenling Yuan , Fengli Li , Zhe Chen , Qiaoxin Xu , Zhenhua Guan , Nanyu Yao , Zhengxi Hu , Junjun Liu , Yuan Zhou , Ying Ye , Yonghui Zhang . AbnI: An α-ketoglutarate-dependent dioxygenase involved in brassicicene CH functionalization and ring system rearrangement. Chinese Chemical Letters, 2024, 35(5): 108788-. doi: 10.1016/j.cclet.2023.108788
3. [3]
  Jing-Qi Tao , Shuai Liu , Tian-Yu Zhang , Hong Xin , Xu Yang , Xin-Hua Duan , Li-Na Guo . Photoinduced copper-catalyzed alkoxyl radical-triggered ring-expansion/aminocarbonylation cascade. Chinese Chemical Letters, 2024, 35(6): 109263-. doi: 10.1016/j.cclet.2023.109263
4. [4]
  Yue Sun , Liming Yang , Yaohang Cheng , Guanghui An , Guangming Li . Pd(I)-catalyzed ring-opening arylation of cyclopropyl-α-aminoamides: Access to α-ketoamide peptidomimetics. Chinese Chemical Letters, 2024, 35(6): 109250-. doi: 10.1016/j.cclet.2023.109250
5. [5]
  Qiuyun Li , Yannan Zhu , Yining Wang , Gang Qi , Wen-Juan Hao , Kelu Yan , Bo Jiang . Catalytic CH activation-initiated transdiannulation: An oxygen transfer route to ring-fluorinated tricyclic γ-lactones. Chinese Chemical Letters, 2024, 35(9): 109494-. doi: 10.1016/j.cclet.2024.109494
6. [6]
  Wenyu Gao , Liming Zhang , Chuang Zhao , Lixiang Liu , Xingran Yang , Jinbo Zhao . Controlled semi-Pinacol rearrangement on a strained ring: Efficient access to multi-substituted cyclopropanes by group migration strategy. Chinese Chemical Letters, 2024, 35(9): 109447-. doi: 10.1016/j.cclet.2023.109447
7. [7]
  Xiaoliu Liang , Chunliu Huang , Hui Liu , Hu Chen , Jiabao Shou , Hongwei Cheng , Gang Liu . Natural hydrogel dressings in wound care: Design, advances, and perspectives. Chinese Chemical Letters, 2024, 35(10): 109442-. doi: 10.1016/j.cclet.2023.109442
8. [8]
  Yingjie Wang , Peng Tang , Wenchao Tu , Qi Gao , Cuizhu Wang , Luying Tan , Lixin Zhao , Hongye Han , Liefeng Ma , Kouharu Otsuki , Weilie Xiao , Wenli Wang , Jinping Liu , Yong Li , Zhajun Zhan , Wei Li , Xianli Zhou , Ning Li . Highly anticipated natural diterpenoids as an important source of new drugs in 2013–2023. Chinese Chemical Letters, 2025, 36(1): 109955-. doi: 10.1016/j.cclet.2024.109955
9. [9]
  Qinghong Zhang , Qiao Zhao , Xiaodi Wu , Li Wang , Kairui Shen , Yuchen Hua , Cheng Gao , Yu Zhang , Mei Peng , Kai Zhao . Visible-light-induced ring-opening cross-coupling of cycloalcohols with vinylazaarenes and enones via β-C-C scission enabled by proton-coupled electron transfer. Chinese Chemical Letters, 2025, 36(2): 110167-. doi: 10.1016/j.cclet.2024.110167
10. [10]
  Jia Chen , Yun Liu , Zerong Long , Yan Li , Hongdeng Qiu . Colorimetric detection of α-glucosidase activity using Ni-CeO₂ nanorods and its application to potential natural inhibitor screening. Chinese Chemical Letters, 2024, 35(9): 109463-. doi: 10.1016/j.cclet.2023.109463
11. [11]
  Deli Chen , Jiawen Li , Xudong Xu , Zhaocui Sun , Yun Yang , Minghui Xu , Hanqiao Liang , Junshan Yang , Hui Meng , Guoxu Ma , Jianhe Wei . Plant-microbial interactions inspired the discovery of novel sesquiterpenoid dimeric skeletons of hidden natural products from Hibiscus tiliaceus. Chinese Chemical Letters, 2024, 35(10): 109451-. doi: 10.1016/j.cclet.2023.109451
12. [12]
  Ying Gao , Rong Zhou , Qiwen Wang , Shaolong Qi , Yuanyuan Lv , Shuang Liu , Jie Shen , Guocan Yu . Natural killer cell membrane doped supramolecular nanoplatform with immuno-modulatory functions for immuno-enhanced tumor phototherapy. Chinese Chemical Letters, 2024, 35(10): 109521-. doi: 10.1016/j.cclet.2024.109521
13. [13]
  Zhilong Xie , Guohui Zhang , Ya Meng , Yefei Tong , Jian Deng , Honghui Li , Qingqing Ma , Shisong Han , Wenjun Ni . A natural nano-platform: Advances in drug delivery system with recombinant high-density lipoprotein. Chinese Chemical Letters, 2024, 35(11): 109584-. doi: 10.1016/j.cclet.2024.109584
14. [14]
  Haobo Wang , Fei Wang , Yong Liu , Zhongxiu Liu , Yingjie Miao , Wanhong Zhang , Guangxin Wang , Jiangtao Ji , Qiaobao Zhang . Emerging natural clay-based materials for stable and dendrite-free lithium metal anodes: A review. Chinese Chemical Letters, 2025, 36(2): 109589-. doi: 10.1016/j.cclet.2024.109589
15. [15]
  Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533
16. [16]
  Huimin Luan , Qinming Wu , Jianping Wu , Xiangju Meng , Feng-Shou Xiao . Templates for the synthesis of zeolites. Chinese Journal of Structural Chemistry, 2024, 43(4): 100252-100252. doi: 10.1016/j.cjsc.2024.100252
17. [17]
  Zhaojun Liu , Zerui Mu , Chuanbo Gao . Alloy nanocrystals: Synthesis paradigms and implications. Chinese Journal of Structural Chemistry, 2023, 42(11): 100156-100156. doi: 10.1016/j.cjsc.2023.100156
18. [18]
  Zhenhao Wang , Yuliang Tang , Ruyu Li , Shuai Tian , Yu Tang , Dehai Li . Bioinspired synthesis of cochlearol B and ganocin A. Chinese Chemical Letters, 2024, 35(7): 109247-. doi: 10.1016/j.cclet.2023.109247
19. [19]
  Hui Jin , Qin Cai , Peiwen Liu , Yan Chen , Derong Wang , Weiping Zhu , Yufang Xu , Xuhong Qian . Multistep continuous flow synthesis of Erlotinib. Chinese Chemical Letters, 2024, 35(4): 108721-. doi: 10.1016/j.cclet.2023.108721
20. [20]
  Caihong Mao , Yanfeng He , Xiaohan Wang , Yan Cai , Xiaobo Hu . Synthesis and molecular recognition characteristics of a tetrapodal benzene cage. Chinese Chemical Letters, 2024, 35(8): 109362-. doi: 10.1016/j.cclet.2023.109362

Get Citation

PDF

XML

Metrics

PDF Downloads(33)
Abstract views(540)
HTML views(123)

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