Citation: Shangfeng Ren, Keke Huang, Jin-Biao Liu, Lianpeng Zhang, Min Hou, Guanyinsheng Qiu. Palladium-catalyzed cyclization of 1-alkynyl-8-iodonaphthalene and double isocyanides for the synthesis of acenaphtho[1,2-b]pyrroles[J]. Chinese Chemical Letters, ;2022, 33(11): 4870-4873. doi: 10.1016/j.cclet.2022.02.028 shu

Palladium-catalyzed cyclization of 1-alkynyl-8-iodonaphthalene and double isocyanides for the synthesis of acenaphtho[1,2-b]pyrroles

Shangfeng Ren ^{a, b, 1} ,
Keke Huang ^{a, 1} ,
Jin-Biao Liu ^{a, *,} ,
Lianpeng Zhang ^{c, *,} ,
Min Hou ^b ,
Guanyinsheng Qiu ^{b, *,}

a.
School of Metallurgical and Chemical Engineering, Jiangxi University of Science and Technology, Ganzhou 341000, China
b.
College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, China
c.
International Joint Research Center for Biomass Materials, Southwest Forestry University, Kunming 650224, China

liujinbiao@jxust.edu.cn

lpz@zju.edu.cn

qiuguanyinsheng@mail.zjxu.edu.cn

Received Date: 26 November 2021
Revised Date: 11 February 2022
Accepted Date: 14 February 2022
Available Online: 18 February 2022

Figures(4)

A palladium-catalyzed formal [2 + 2 + 1] cyclization of 1-alkynyl-8-iodonaphthalene with double isocyanides is developed herein. The transformation worked well to produce a series of 7H-acenaphtho[1,2-b]pyrrole with a broad reaction scope. Isocyanides play a dual role in the reaction. One is a C1 building block, and another is used as C1N1 component. In the process, the [2 + 2 + 1] cyclization involves imidoylation, regioselective addition of imidoylpalladium species into alkyne, double imidoylation, and another addition of the resulting imidoylpalladium species into imine bonds.
- [2 + 2 + 1] Cyclization,
- Isocyanides,
- Palladium catalysis,
- Alkyne,
- Pyrrole
1. [1]
  J. Collet, T. Roose, E. Ruijter, et al., Angew. Chem. Int. Ed. 59 (2020) 540–558. doi: 10.1002/anie.201905838
2. [2]
  Z. Gu, S. Ji, Acta Chim. Sin. 76 (2018) 347–356. doi: 10.6023/A18010023
3. [3]
  L. Ackermann, Acc. Chem. Res. 53 (2020) 84–104.
4. [4]
  N. Liu, L. Zhou, Z. Wu, Acc. Chem. Res. 54 (2021) 3953–3967. doi: 10.1021/acs.accounts.1c00489
5. [5]
  C. Caboon, C. Bielawski, Coord. Chem. Rev. 374 (2018) 261–278. doi: 10.1016/j.ccr.2018.06.017
6. [6]
  J. Wang, D. Li, Q. Zhu, Org. Biomol. Chem. 19 (2021) 6730–6745. doi: 10.1039/D1OB00864A
7. [7]
  J. Collet, T. Roose, B. Weijers, et al., Molecules 25 (2020) 4906–4958. doi: 10.3390/molecules25214906
8. [8]
  S. Shaifali, P. Das, Chem. Rec. (2021), doi: 10.1002/tcr.202100157. doi: 10.1002/tcr.202100157
9. [9]
  Y. Shi, C. Xia, Y. Huang, Chem. Asian J. 16 (2021) 2830–2841. doi: 10.1002/asia.202100800
10. [10]
  P. Das, B. Bhanage, Adv. Synth. Catal. 362 (2020) 3022–3058. doi: 10.1002/adsc.202000245
11. [11]
  Z. Yin, J. Xu, X.F. Wu, ACS. Catal. 10 (2020) 6510–6531. doi: 10.1021/acscatal.0c01479
12. [12]
  B. Song, B. Xu, Chem. Soc. Rev. 46 (2017) 1103–1123. doi: 10.1039/C6CS00384B
13. [13]
  J. Lei, J. Huang, Q. Zhu, Org. Biomol. Chem. 14 (2016) 2593–2602. doi: 10.1039/C6OB00087H
14. [14]
  B. Zhang, A. Studer, Chem. Soc. Rev. 44 (2015) 3505–3521. doi: 10.1039/C5CS00083A
15. [15]
  Y. Liu, S.J. Li, X.L. Chen, et al., Adv. Synth. Catal. 362 (2020) 688–694. doi: 10.1002/adsc.201901300
16. [16]
  G. Gomes, Y. Loginova, S. Vatsadze, et al., J. Am. Chem. Soc. 140 (2018) 14272–14288. doi: 10.1021/jacs.8b08513
17. [17]
  T. Mitamura, K. Iwata, A. Ogawa, J. Org. Chem. 76 (2011) 3880–3887. doi: 10.1021/jo200299d
18. [18]
  S. Chen, M. Oliva, L. Van Meervelt, et al., Adv. Synth. Catal. 363 (2020) 3220–3226.
19. [19]
  La-ongthong Kannika, P. Naweephattana, O. Khaikate, et al., J. Org. Chem. 85 (2020) 6338–6351. doi: 10.1021/acs.joc.0c00003
20. [20]
  O. Khaikate, D. Soorukram, P. Leowanawat, et al., Eur. J. Org. Chem. 2019 (2019) 7050–7057. doi: 10.1002/ejoc.201901209
21. [21]
  Y. Zhang, Y. Jin, Y. Wang, et al., Green Chem. 23 (2021) 6926–6930. doi: 10.1039/D1GC02670D
22. [22]
  Y. Liu, J.L. Li, X.G. Liu, et al., Org. Lett. 23 (2021) 1891–1897. doi: 10.1021/acs.orglett.1c00309
23. [23]
  Y. Liu, X.L. Chen, X.Y. Li, et al., J. Am. Chem. Soc. 143 (2021) 964–972. doi: 10.1021/jacs.0c11138
24. [24]
  Y. Yuan, S.Y. Zhang, W.H. Dong, et al., Adv. Synth. Catal. 363 (2021) 4216–4221.
25. [25]
  C. Tran, S.I. Kawaguchi, F. Sato, et al., J. Org. Chem. 85 (2020) 7258–7266. doi: 10.1021/acs.joc.0c00647
26. [26]
  Y. Liu, X.L. Chen, F.L. Zeng, et al., J. Org. Chem. 83 (2018) 11727–11735. doi: 10.1021/acs.joc.8b01657
27. [27]
  X. Sun, W. Wang, Y. Li, et al., Org. Lett. 18 (2016) 4638–4641. doi: 10.1021/acs.orglett.6b02271
28. [28]
  X. Sun, W. Wang, M. Jia, et al., Acta Chim. Sin. 75 (2017) 115–118. doi: 10.6023/A16090480
29. [29]
  N. Tsukada, M. Wada, N. Takahashi, et al., J. Organometallic Chem. 694 (2009) 1333–1338. doi: 10.1016/j.jorganchem.2008.12.039
30. [30]
  G. Qiu, Q. Wang, J. Zhu, Org. Lett. 19 (2017) 270–273. doi: 10.1021/acs.orglett.6b03592
31. [31]
  J. Peng, Y. Gao, W. Hu, et al., Org. Lett. 18 (2016) 5924–5927. doi: 10.1021/acs.orglett.6b02999
32. [32]
  K. Huang, J.B. Liu, Z. Chen, et al., Org. Lett. 22 (2020) 5931–5935. doi: 10.1021/acs.orglett.0c02019
33. [33]
  Y. Zhang, W. Lai, L. Zhang, et al., Org. Biomol. Chem. 19 (2021) 1827–1834. doi: 10.1039/D0OB02233K
34. [34]
  K. Majeed, B. Liu, F. Zhou, et al., Synthesis (Mass) 53 (2021) 2103–2113.
35. [35]
  Y.C. Hsieh, T.C. Wu, J.Y. Li, et al., Org. Lett. 18 (2016) 1868–1871. doi: 10.1021/acs.orglett.6b00637
36. [36]
  J. Wallbaum, R. Neufeld, D. Stalke, et al., Angew Chem. Int. Ed. 52 (2013) 13243–13246. doi: 10.1002/anie.201307793
37. [37]
  G.Y. Zhu, T.Y. Zhai, X. Li, et al., Org. Lett. 23 (2021) 8067–8071.
38. [38]
  P. Smith, Y. Jiang, Z. Tang, et al., Org. Lett. 23 (2021) 6547–6552. doi: 10.1021/acs.orglett.1c02360
39. [39]
  D. Campeau, A. Pommainville, F. Gagosz, J. Am. Chem. Soc. 143 (2021) 9601–9611. doi: 10.1021/jacs.1c04051
40. [40]
  Y. Zhou, L. Zhou, L. Jesikiewicz, et al., J. Am. Chem. Soc. 142 (2020) 9908–9914. doi: 10.1021/jacs.0c03859
41. [41]
  Y. Shan, L. Su, D. Chen, et al., Chin. Chem. Lett. 32 (2021) 437–440. doi: 10.1016/j.cclet.2020.04.041
42. [42]
  K. Zhou, J. Huang, J. Wu, et al., Chin. Chem. Lett. 32 (2021) 37–39. doi: 10.1016/j.cclet.2020.11.049
43. [43]
  D. Chen, M. Yang, J. Li, P. Cui, et al., J. Org. Chem. 85 (2020) 6441–6449. doi: 10.1021/acs.joc.0c00323
44. [44]
  X. Chen, G. Qiu, R. Liu, et al., Org. Chem. Front. 7 (2020) 890–895.
45. [45]
  D. Chen, Y. Shan, J. Li, et al., Org. Lett. 21 (2019) 4044–4048. doi: 10.1021/acs.orglett.9b01220
46. [46]
  Y. Wu, J.Y. Chen, J. Ning, et al., Green Chem. 23 (2021) 3950–3954. doi: 10.1039/D1GC00562F
47. [47]
  Q.W. Gui, F. Teng, Z.C. Lia, et al., Chin. Chem. Lett. 32 (2021) 1907–1910. doi: 10.1016/j.cclet.2021.01.021
48. [48]
  J. Jiang, Z. Wang, W.M. He, Chin. Chem. Lett. 32 (2021) 1591–1592. doi: 10.1016/j.cclet.2021.02.067
49. [49]
  W.B. He, L.Q. Gao, X.J. Chen, et al., Chin. Chem. Lett. 31 (2020) 1895–1898.
50. [50]
  D. Prat, A. Wells, J. Hayler, et al., Green. Chem. 18 (2016) 288–296. doi: 10.1039/C5GC01008J
1. [1]
  Anjing Liao , Wei Sun , Yaming Liu , Han Yan , Zhi Xia , Jian Wu . Pyrrole and pyrrolidine analogs: The promising scaffold in discovery of pesticides. Chinese Chemical Letters, 2025, 36(3): 110094-. doi: 10.1016/j.cclet.2024.110094
2. [2]
  Yunqiang Li , Yongxian Huang , Sinuo Li , He Huang , Zhiwei Jiao . Elaborating azaaryl alkanes enabled by photoredox/palladium dual catalyzed dialkylation of azaaryl alkenes. Chinese Chemical Letters, 2025, 36(4): 110051-. doi: 10.1016/j.cclet.2024.110051
3. [3]
  Baokang Geng , Xiang Chu , Li Liu , Lingling Zhang , Shuaishuai Zhang , Xiao Wang , Shuyan Song , Hongjie Zhang . High-efficiency PdNi single-atom alloy catalyst toward cross-coupling reaction. Chinese Chemical Letters, 2024, 35(7): 108924-. doi: 10.1016/j.cclet.2023.108924
4. [4]
  Zhao Gu , Yunhui Yang , Song Ye , Congyang Wang . 2,3-Arylacylation of allenes through synergetic catalysis of palladium and N-heterocyclic carbene. Chinese Chemical Letters, 2025, 36(5): 110334-. doi: 10.1016/j.cclet.2024.110334
5. [5]
  Ke Zhang , Sheng Zuo , Pengyuan You , Tong Ru , Fen-Er Chen . Palladium-catalyzed stereoselective decarboxylative [4 + 2] cyclization of 2-methylidenetrimethylene carbonates with pyrrolidone-derived enones: Straightforward access to chiral tetrahydropyran-fused spiro-pyrrolidine-2,3-diones. Chinese Chemical Letters, 2024, 35(6): 109157-. doi: 10.1016/j.cclet.2023.109157
6. [6]
  Zhuwen Wei , Jiayan Chen , Congzhen Xie , Yang Chen , Shifa Zhu . Divergent de novo construction of α-functionalized pyrrole derivatives via coarctate reaction. Chinese Chemical Letters, 2024, 35(12): 109677-. doi: 10.1016/j.cclet.2024.109677
7. [7]
  Jian-Rong Li , Jieying Hu , Lai-Hon Chung , Jilong Zhou , Parijat Borah , Zhiqing Lin , Yuan-Hui Zhong , Hua-Qun Zhou , Xianghua Yang , Zhengtao Xu , Jun He . Insight into stable, concentrated radicals from sulfur-functionalized alkyne-rich crystalline frameworks and application in solar-to-vapor conversion. Chinese Journal of Structural Chemistry, 2024, 43(8): 100380-100380. doi: 10.1016/j.cjsc.2024.100380
8. [8]
  Yaping Zhang , Wei Zhou , Mingchun Gao , Tianqi Liu , Bingxin Liu , Chang-Hua Ding , Bin Xu . Oxidative cyclization of allyl compounds and isocyanide: A facile entry to polysubstituted 2-cyanopyrroles. Chinese Chemical Letters, 2024, 35(4): 108836-. doi: 10.1016/j.cclet.2023.108836
9. [9]
  Yuhao Guo , Na Li , Tingjiang Yan . Tandem catalysis for photoreduction of CO2 into multi-carbon fuels on atomically thin dual-metal phosphochalcogenides. Chinese Journal of Structural Chemistry, 2024, 43(7): 100320-100320. doi: 10.1016/j.cjsc.2024.100320
10. [10]
  Yi Luo , Lin Dong . Multicomponent remote C(sp²)-H bond addition by Ru catalysis: An efficient access to the alkylarylation of 2H-imidazoles. Chinese Chemical Letters, 2024, 35(10): 109648-. doi: 10.1016/j.cclet.2024.109648
11. [11]
  Xiangyang Ji , Yishuang Chen , Peng Zhang , Shaojia Song , Jian Liu , Weiyu Song . Boosting the first C–H bond activation of propane on rod-like V/CeO₂ catalyst by photo-assisted thermal catalysis. Chinese Chemical Letters, 2025, 36(5): 110719-. doi: 10.1016/j.cclet.2024.110719
12. [12]
  Xiaohui Fu , Yanping Zhang , Juan Liao , Zhen-Hua Wang , Yong You , Jian-Qiang Zhao , Mingqiang Zhou , Wei-Cheng Yuan . Palladium-catalyzed enantioselective decarboxylation of vinyl cyclic carbamates: Generation of amide-based aza-1,3-dipoles and application to asymmetric 1,3-dipolar cycloaddition. Chinese Chemical Letters, 2024, 35(12): 109688-. doi: 10.1016/j.cclet.2024.109688
13. [13]
  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
14. [14]
  Jinge Zhu , Ailing Tang , Leyi Tang , Peiqing Cong , Chao Li , Qing Guo , Zongtao Wang , Xiaoru Xu , Jiang Wu , Erjun Zhou . Chlorination of benzyl group on the terminal unit of A₂-A₁-D-A₁-A₂ type nonfullerene acceptor for high-voltage organic solar cells. Chinese Chemical Letters, 2025, 36(1): 110233-. doi: 10.1016/j.cclet.2024.110233
15. [15]
  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
16. [16]
  Conghui Wang , Lei Xu , Zhenhua Jia , Teck-Peng Loh . Recent applications of macrocycles in supramolecular catalysis. Chinese Chemical Letters, 2024, 35(4): 109075-. doi: 10.1016/j.cclet.2023.109075
17. [17]
  Wei Chen , Pieter Cnudde . A minireview to ketene chemistry in zeolite catalysis. Chinese Journal of Structural Chemistry, 2024, 43(11): 100412-100412. doi: 10.1016/j.cjsc.2024.100412
18. [18]
  Lin Zhang , Chaoran Li , Thongthai Witoon , Xingda An , Le He . Nano-thermometry in photothermal catalysis. Chinese Journal of Structural Chemistry, 2025, 44(4): 100456-100456. doi: 10.1016/j.cjsc.2024.100456
19. [19]
  Gangsheng Li , Xiang Yuan , Fu Liu , Zhihua Liu , Xujie Wang , Yuanyuan Liu , Yanmin Chen , Tingting Wang , Yanan Yang , Peicheng Zhang . Three-step synthesis of flavanostilbenes with a 2-cyclohepten-1-one core by Cu-mediated [5 + 2] cycloaddition/decarboxylation cascade. Chinese Chemical Letters, 2025, 36(2): 109880-. doi: 10.1016/j.cclet.2024.109880
20. [20]
  Yu Xiong , Li-Jun Hu , Jian-Guo Song , Di Zhang , Yi-Shuang Peng , Xiao-Jun Huang , Jian Hong , Bin Zhu , Wen-Cai Ye , Ying Wang . Structure elucidation of plumerubradins A–C: Correlations between ¹H NMR signal patterns and structural information of [2+2]-type cyclobutane derivatives. Chinese Chemical Letters, 2025, 36(5): 110149-. doi: 10.1016/j.cclet.2024.110149

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(881)
HTML views(193)

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