Citation: Pei Xu, Yi-Ming Zhu, Xin-Yu Liu, Xiao-Zhou Zhou, Shun-Yi Wang, Shun-Jun Ji. Mn(Ⅲ)-mediated radical reaction of 2-isocyano-6-alkenyl(alkynyl) benzonitriles with arylboronic acids: Synthesis of pyrroloisoquinoline derivatives[J]. Chinese Chemical Letters, ;2021, 32(1): 413-416. doi: 10.1016/j.cclet.2020.03.023 shu

Mn(Ⅲ)-mediated radical reaction of 2-isocyano-6-alkenyl(alkynyl) benzonitriles with arylboronic acids: Synthesis of pyrroloisoquinoline derivatives

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, China

shunyi@suda.edu.cn

shunjun@suda.edu.cn

Received Date: 19 January 2020
Revised Date: 17 February 2020
Accepted Date: 7 March 2020
Available Online: 9 March 2020

Figures(5)

A Mn(Ⅲ) mediated radical reaction of new designed multi-functionalized 2-isocyano-6-alkenyl(alkynyl) benzonitriles with arylboronic acids has been developed. This reaction provides a method for the synthesis of pyrroloisoquinoline derivatives through the formation of two C—C bonds and one C—N bond via radical cascade cyclization in one step.
- 2-Isocyano-6-alkenyl(alkynyl)benzonitriles,
- Arylboronic acids,
- Pyrroloisoquinoline derivatives,
- Radical reaction
1. [1]
  (a) M.X. Wang, Acc. Chem. Res. 48 (2015) 602-611;
  (b) P. Anbarasan, T. Schareina, M. Beller, Chem. Soc. Rev. 40 (2011) 5049-5067.
2. [2]
  (a) S.S. Wang, H. Fu, Y. Shen, M. Sun, Y.M. Li, J. Org. Chem. 81 (2016) 2920-2929;
  (b) X.T. Zhu, Q. Zhao, F. Liu, et al., Chem. Commun. 53 (2017) 6828-6831;
  (c) J. Yu, H.X. Sheng, S.W. Wang, et al., Chem. Commun. 55 (2019) 4578-4581.
3. [3]
  (a) J. Zheng, Y. Zhang, D. Wang, S. Cui, Org. Lett. 18 (2016) 1768-1771;
  (b) X. Li, X. Fang, S. Zhuang, P. Liu, P. Sun, Org. Lett. 19 (2017) 3580-3583;
  (c) L.J. Wu, Y. Yang, R.J. Song, et al., Chem. Commun. 54 (2018) 1367-1370;
  (d) X.H. Shan, H.X. Zheng, B. Yang, et al., Nat. Commun. 10 (2019) 908.
4. [4]
  (a) Z. Wu, R. Ren, C. Zhu, Angew. Chem. Int. Ed. 55 (2016) 10821-10824;
  (b) N. Wang, L. Li, Z.L. Li, et al., Org. Lett. 18 (2016) 6026-6029;
  (c) Y. Chen, J. Du, Z. Zuo, Chem 6 (2020) 266-279.
5. [5]
  (a) B. Song, B. Xu, Chem. Soc. Rev. 46 (2017) 1103-1123;
  (b) P. Xu, F. Wang, T.Q. Wei, et al., Org. Lett. 19 (2017) 4484;
  (c) Y. Fang, J.M. Yang, R. Zhang, S.Y. Wang, S.J. Ji, Org. Chem. Front. 6 (2019) 3383-3386;
  (d) P. Xu, Y.M. Zhu, X.J. Li, et al., Adv. Synth. Catal. 361 (2019) 4909-4913;
  (e) G.S. Chen, S.J. Chen, J. Luo, et al., Angew. Chem. Int. Ed. 59 (2020) 614-621.
6. [6]
  (a) B. Zhang, A. Studer, Chem. Soc. Rev. 44 (2015) 3505-3521;
  (b) J.J. Cao, T.H. Zhu, S.Y. Wang, et al., Chem. Commun. 50 (2014) 6439-6442;
  (c) J.J. Cao, X. Wang, S.Y. Wang, S.J. Ji, Chem. Commun. 50 (2014) 12892-12895;
  (d) Y. Fang, C. Liu, F. Wang, et al., Org. Chem. Front. 6 (2019) 660-663.
7. [7]
  (a) M. Tobisu, K. Koh, T. Furukawa, N. Chatani, Angew. Chem. Int. Ed. 51 (2012) 11363-11366;
  (b) Y. Li, T. Miao, P. Li, L. Wang, Org. Lett. 20 (2018) 1735-1739;
  (c) A. Guo, J.B. Han, X.Y. Tang, Org. Lett. 20 (2018) 2351-2355;
  (d) J. Wei, D. Gu, S. Wang, et al., Org. Chem. Front. 5 (2018) 2568-2572;
  (e) S. Liu, F. Fan, N. Wang, et al., Adv. Synth. Catal. 361 (2019) 3086-3093;
  (f) S. Liu, W. Pan, S. Wu, et al., Green Chem. 21 (2019) 2905-2910.
8. [8]
  (a) B. Zhang, A. Studer, Org. Lett. 16 (2014) 1216-1219;
  (b) C.J. Evoniuk, M. Ly, I.V. Alabugin, Chem. Commun. 51 (2015) 12831-12834.
9. [9]
  T. Mitamura, K. Iwata, A. Ogawa, Org. Lett. 11 (2009) 3422-3424. doi: 10.1021/ol901267h
10. [10]
  (a) D. Li, T. Mao, J. Huang, Q. Zhu, Org. Lett. 19 (2017) 3223-3226;
  (b) D. Li, J. Lei, Org. Biomol. Chem. 17 (2019) 9666-9671.
11. [11]
  (a) D. Leifert, A. Studer, Angew. Chem. Int. Ed. 55 (2016) 11660-11663;
  (b) X. Sun, W. Wang, Y. Li, J. Ma, S. Yu, Org. Lett. 18 (2016) 4638-4641;
  (c) Y. Liu, X.L. Chen, F.L. Zeng, et al., J. Org. Chem. 83 (2018) 11727-11735;
  (d) Y. Fang, C. Liu, W. Rao, S.Y. Wang, S.J. Ji, Org. Lett. 21 (2019) 7687-7691.
12. [12]
  (a) W.C. Yang, K. Wei, X. Sun, J. Zhu, L. Wu, Org. Lett. 20 (2018) 3144-3147;
  (b) Y. Yuan, W. Dong, X. Gao, X. Xie, Z. Zhang, Org. Lett. 21 (2019) 469-472;
  (c) K. Luo, W.C. Yang, K. Wei, et al., Org. Lett. 21 (2019) 7851-7856;
  (d) Y. Liu, X.L. Chen, K. Sun, et al., Org. Lett. 21 (2019) 4019-4024.
13. [13]
  M. Suginome, T. Fukuda, Y. Ito, Org. Lett. 1 (1999) 1977-1979. doi: 10.1021/ol991133w
14. [14]
  P. Xu, Y.M. Zhu, F. Wang, S.Y. Wang, S.J. Ji, Org. Lett. 21 (2019) 683-686.
1. [1]
  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
2. [2]
  Yifan LIU , Zhan ZHANG , Rongmei ZHU , Ziming QIU , Huan PANG . A three-dimensional flower-like Cu-based composite and its low-temperature calcination derivatives for efficient oxygen evolution reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 979-990. doi: 10.11862/CJIC.20240008
3. [3]
  Yu-Yu Tan , Lin-Heng He , Wei-Min He . Copper-mediated assembly of SO₂F group via radical fluorine-atom transfer strategy. Chinese Chemical Letters, 2024, 35(9): 109986-. doi: 10.1016/j.cclet.2024.109986
4. [4]
  Jingtai Bi , Yupeng Cheng , Mengmeng Sun , Xiaofu Guo , Shizhao Wang , Yingying Zhao . Efficient and selective photocatalytic nitrite reduction to N₂ through CO₂ anion radical by eco-friendly tartaric acid activation. Chinese Chemical Letters, 2024, 35(11): 109639-. doi: 10.1016/j.cclet.2024.109639
5. [5]
  Ping Sun , Yuanqin Huang , Shunhong Chen , Xining Ma , Zhaokai Yang , Jian Wu . Indole derivatives as agrochemicals: An overview. Chinese Chemical Letters, 2024, 35(7): 109005-. doi: 10.1016/j.cclet.2023.109005
6. [6]
  Zhengzhong Zhu , Shaojun Hu , Zhi Liu , Lipeng Zhou , Chongbin Tian , Qingfu Sun . A cationic radical lanthanide organic tetrahedron with remarkable coordination enhanced radical stability. Chinese Chemical Letters, 2025, 36(2): 109641-. doi: 10.1016/j.cclet.2024.109641
7. [7]
  Bairu Meng , Zongji Zhuo , Han Yu , Sining Tao , Zixuan Chen , Erik De Clercq , Christophe Pannecouque , Dongwei Kang , Peng Zhan , Xinyong Liu . Design, synthesis, and biological evaluation of benzo[4,5]thieno[2,3-d]pyrimidine derivatives as novel HIV-1 NNRTIs. Chinese Chemical Letters, 2024, 35(6): 108827-. doi: 10.1016/j.cclet.2023.108827
8. [8]
  Shuo Li , Xinran Liu , Yongjie Zheng , Jun Ma , Shijie You , Heshan Zheng . Effective peroxydisulfate activation by CQDs-MnFe₂O₄@ZIF-8 catalyst for complementary degradation of bisphenol A by free radicals and non-radical pathways. Chinese Chemical Letters, 2024, 35(5): 108971-. doi: 10.1016/j.cclet.2023.108971
9. [9]
  Peng Wang , Jianjun Wang , Ni Song , Xin Zhou , Ming Li . Radical dehydroxymethylative fluorination of aliphatic primary alcohols and diverse functionalization of α-fluoroimides via BF₃·OEt₂-catalyzed C‒F bond activation. Chinese Chemical Letters, 2025, 36(1): 109748-. doi: 10.1016/j.cclet.2024.109748
10. [10]
  Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
11. [11]
  Jing Cao , Dezheng Zhang , Bianqing Ren , Ping Song , Weilin Xu . Mn incorporated RuO₂ nanocrystals as an efficient and stable bifunctional electrocatalyst for oxygen evolution reaction and hydrogen evolution reaction in acid and alkaline. Chinese Chemical Letters, 2024, 35(10): 109863-. doi: 10.1016/j.cclet.2024.109863
12. [12]
  Yulong Shi , Fenbei Chen , Mengyuan Wu , Xin Zhang , Runze Meng , Kun Wang , Yan Wang , Yuheng Mei , Qionglu Duan , Yinghong Li , Rongmei Gao , Yuhuan Li , Hongbin Deng , Jiandong Jiang , Yanxiang Wang , Danqing Song . Chemical construction and anti-HCoV-OC43 evaluation of novel 10,12-disubstituted aloperine derivatives as dual cofactor inhibitors of TMPRSS2 and SR-B1. Chinese Chemical Letters, 2024, 35(5): 108792-. doi: 10.1016/j.cclet.2023.108792
13. [13]
  Fangwen Peng , Zhen Luo , Yingjin Ma , Haibo Ma . Theoretical study of aromaticity reversal in dimethyldihydropyrene derivatives. Chinese Journal of Structural Chemistry, 2024, 43(5): 100273-100273. doi: 10.1016/j.cjsc.2024.100273
14. [14]
  Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
15. [15]
  Zizhuo Liang , Fuming Du , Ning Zhao , Xiangxin Guo . Revealing the reason for the unsuccessful fabrication of Li3Zr2Si2PO12 by solid state reaction. Chinese Journal of Structural Chemistry, 2023, 42(11): 100108-100108. doi: 10.1016/j.cjsc.2023.100108
16. [16]
  Jindian Duan , Xiaojuan Ding , Pui Ying Choy , Binyan Xu , Luchao Li , Hong Qin , Zheng Fang , Fuk Yee Kwong , Kai Guo . Oxidative spirolactonisation for modular access of γ-spirolactones via a radical tandem annulation pathway. Chinese Chemical Letters, 2024, 35(10): 109565-. doi: 10.1016/j.cclet.2024.109565
17. [17]
  Xiao-Bo Liu , Ren-Ming Liu , Xiao-Di Bao , Hua-Jian Xu , Qi Zhang , Yu-Feng Liang . Nickel-catalyzed reductive formylation of aryl halides via formyl radical. Chinese Chemical Letters, 2024, 35(12): 109783-. doi: 10.1016/j.cclet.2024.109783
18. [18]
  Chaozheng He , Jia Wang , Ling Fu , Wei Wei . Nitric oxide assists nitrogen reduction reaction on 2D MBene: A theoretical study. Chinese Chemical Letters, 2024, 35(5): 109037-. doi: 10.1016/j.cclet.2023.109037
19. [19]
  Yiqian Jiang , Zihan Yang , Xiuru Bi , Nan Yao , Peiqing Zhao , Xu Meng . Mediated electron transfer process in α-MnO₂ catalyzed Fenton-like reaction for oxytetracycline degradation. Chinese Chemical Letters, 2024, 35(8): 109331-. doi: 10.1016/j.cclet.2023.109331
20. [20]
  Yu-Hang Miao , Zheng-Xu Zhang , Xu-Yi Huang , Yuan-Zhao Hua , Shi-Kun Jia , Xiao Xiao , Min-Can Wang , Li-Ping Xu , Guang-Jian Mei . Catalytic asymmetric dearomative azo-Diels–Alder reaction of 2-vinlyindoles. Chinese Chemical Letters, 2024, 35(4): 108830-. doi: 10.1016/j.cclet.2023.108830

Get Citation

PDF

XML

Metrics

PDF Downloads(5)
Abstract views(847)
HTML views(116)

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