Citation: Feng Yadong, Liu Ying, Fu Qi, Zou Zhongai, Shen Jinhai, Cui Xiuling. Construction of diaminobenzoquinone imines via ferrocene-initiated radical reaction of benzoquinone with amines[J]. Chinese Chemical Letters, ;2020, 31(3): 733-735. doi: 10.1016/j.cclet.2019.09.026 shu

Construction of diaminobenzoquinone imines via ferrocene-initiated radical reaction of benzoquinone with amines

Feng Yadong ^a,b,*, ,
Liu Ying ^a ,
Fu Qi ^a ,
Zou Zhongai ^a ,
Shen Jinhai ^a ,
Cui Xiuling ^b,*,

a.
College of Environment and Public Health, Xiamen Huaxia University, Xiamen 361024, China
b.
Engineering Research Center of Molecular Medicine of Ministry of Education, Key Laboratory of Fujian Molecular Medicine, Key Laboratory of Xiamen Marine and Gene Drugs, School of Biomedical Sciences, Huaqiao University, Xiamen 361021, China

fengyd@hxxy.edu.cn

cuixl@hqu.edu.cn

Received Date: 24 July 2019
Revised Date: 9 September 2019
Accepted Date: 12 September 2019
Available Online: 12 September 2019

Figures(3)

A ferrocene-initiated radical reaction of benzoquinone with amines has been successfully developed for the direct access to diaminobenzoquinone imines in high yields, in which the commercially available and cheap ferrocene was employed as a radical initiator and TBHP was used as an oxidant. Moreover, this reaction could be achieved with low loading of ferrocene (0.5 mol%). This protocol is highly efficient with good substrate tolerance and provides a new approach for the construction of benzoquinone imines with potential pharmaceutical interest.
- Benzoquinone imines,
- Ferrocene-initiated,
- Radical process,
- Benzoquinone,
- Amines
1. [1]
  (a) E. Prochazka, B.I. Escher, M.J. Plewa, F.D.L. Leusch, Chem. Res. Toxicol. 28 (2015) 2059-2068;
  (b) R. Mout, Z.D. Xu, A.K.H. Wolf, V.J. Davisson, G.K. Jarori, Malar. J.11 (2012) 54-54;
  (c) D. Tasdemir, R. Brun, V. Yardley, S.G. Franzblau, P. Ruedi, Chem. Biodiv. 3 (2006) 1230-1237;
  (d) L.F. Fieser, E.M. Chamberlin, J. Am. Chem. Soc. 70 (1948) 71-75;
  (e) B. Joy, S.N. Kumar, M.S. Soumya, et al., Phytomedicine 21 (2014) 1292-1297;
  (f)A.Cavalli, M.L.Bolognesi, S.Capsoni, etal., Angew.Chem.Int.Ed.46 (2007)3689-3692;
  (g) T.J. Monks, P. Hanzlik, G.M. Cohen, D. Ross, D.G. Graham, Toxicol. Appl. Pharmacol. 112 (1992) 2-16.
2. [2]
  (a) J. Yu, H. Zhang, Q. Lu, et al., Chem. Ind. Eng. Progress 34 (2015) 1115-1121;
  (b) M.R. Halhalli, B. Sellergren, Polym. Chem. 6 (2015) 7320-7332;
  (c) M.A. Hanna, M.M. Girges, Acta Polym. 41 (1990) 354-360;
  (d) S. Rajappa, S.J. Shenoy, Tetrahedron 42 (1986) 5739-5746.
3. [3]
  S. Rajappa, R. Sreenivasan, A.V. Rane, Tetrahedron Lett. 24 (1983) 3155-3158. doi: 10.1016/S0040-4039(00)88121-6
4. [4]
  V. Nair, C. Rajesh, R. Dhanya, A.U. Vinod, Tetrahedron Lett. 42 (2001) 2045-2046. doi: 10.1016/S0040-4039(01)00072-7
5. [5]
  V. Nair, R. Dhanya, S. Viji, Tetrahedron 61 (2005) 5843-5848. doi: 10.1016/j.tet.2005.04.008
6. [6]
  K.A. Parker, T.L. Mindt, Org. Lett. 4 (2002) 4265-4268. doi: 10.1021/ol026849x
7. [7]
  (a) Y. Park, Y. Kim, S. Chang, Chem. Rev. 117 (2017) 9247-9301;
  (b) J. Kim, S. Chang, Angew. Chem. Int. Ed. 53 (2014) 2203-2207;
  (c) T. Kang, Y. Kim, D. Lee, Z. Wang, S. Chang, J. Am. Chem. Soc.136 (2014) 4141-4144;
  (d) H. Hwang, J. Kim, J. Jeong, S. Chang, J. Am. Chem. Soc. 136 (2014) 10770-10776;
  (e) C. Pi, X. Cui, Y. Wu, J. Org. Chem. 80 (2015) 7333-7339;
  (f) M.E. Wei, L.H. Wang, Y.Y. Li, X. Cui, Chin. Chem. Lett. 26 (2015) 1336-1340;
  (g) X. Han, P. Lin, Q. Li, Chin. Chem. Lett. 30 (2019) 1495-1502;
  (h) S. Yuan, S. Wang, M. Zhao, et al., Chin. Chem. Lett. 31 (2020) 349-352;
  (i) Q. Huang, L. Zhu, D. Yi, X. Zhao, W. Wei, Chin. Chem. Lett. 31 (2020) 373-376;
  (j) X. Zhang, S. Dong, Q. Ding, X. Fan, G. Zhang, Chin.Chem. Lett. 30 (2019) 375-378;
  (k) L. Xie, S. Peng, L. Jiang, et al., Org. Chem. Front. 6 (2019) 167-171;
  (l) L. Xie, S. Peng, F. Liu, et al., ACS Sustainable Chem. Eng. 7 (2019) 7193-7199.
8. [8]
  J.A. Jordan-Hore, C.C.C. Johansson, M. Gulias, E.M. Beck, M.J. Gaunt, J. Am. Chem. Soc. 130 (2008) 16184-16186. doi: 10.1021/ja806543s
9. [9]
  S.M. Paradine, M.C. White, J. Am. Chem. Soc. 134 (2012) 2036-2039. doi: 10.1021/ja211600g
10. [10]
  (a) Y. Feng, Y. Li, Y. Yu, L. Wang, X. Cui, RSC Adv. 8 (2018) 8450-8454;
  (b) Y. Feng, Z. Zhang, Q. Fu, et al., Chin. Chem. Lett. 31 (2020) 58-60.
11. [11]
  (a) C. Liu, D. Liu, A. Lei, Acc. Chem. Res. 47 (2014) 3459-3470;
  (b) S.A. Girard, T. Knauber, C.J. Li, Angew. Chem. Int. Ed. 53 (2014) 74-100;
  (c) R. Braslau, M.O. Anderson, F. Rivera, et al., Tetrahedron 58 (2002) 5513-5523;
  (d) S. Bath, N.M. Laso, H. Lopez-Ruiz, B. Quiclet-Sire, S.Z. Zard, Chem. Commun. 34 (2003) 204-205;
  (e) J. Wang, C. Liu, J. Yuan, A. Lei, Angew. Chem. Int. Ed. 52 (2013) 2256-2259;
  (f) J. Xie, J. Yu, M. Rudolph, F. Rominger, A.S. Hashmi, Angew. Chem. Int. Ed. 55 (2016) 9416-9421;
  (g) C. Wang, J. Qin, X. Shen, et al., Angew. Chem. Int. Ed. 55 (2016) 685-688;
  (h) L.Y. Xie, S. Peng, F. Liu, et al., Org. Chem. Front. 5 (2018) 2604-2609;
  (i) L.Y. Xie, S. Peng, F. Liu, et al., Adv. Synth. Catal. 360 (2018) 4259-4264;
  (j) L. Xie, T. Fang, J. Tan, et al., Green Chem. 21 (2019) 3858-3863.
12. [12]
  (a) D. Leifert, C.G. Daniliuc, A. Studer, Org. Lett. 15 (2013) 6286-6289;
  (b) S. Wertz, D. Leifert, A. Studer, Org. Lett. 15 (2013) 928-931.
13. [13]
  Y. Feng, H. Zhang, Y. Yu, L. Yang, X. Cui, Eur. J. Org. Chem. 16 (2019) 2740-2744.
14. [14]
  (a) L. Wang, D. Xiong, L. Jie, C. Yu, X. Cui, Chin. Chem. Lett. 29 (2018) 907-910;
  (b) L. Xu, T. Li, L. Wang, X. Cui, J. Org. Chem. 84 (2019) 560-567;
  (c) Z. Yang, L. Jie, Z. Yao, et al., Adv. Catal. Synth. 1 (2019) 214-258;
  (d) P. Chao, X. Yin, X. Cui, Y. Ma, Y. Wu, Org. Lett. 7 (2019) 2081-2084;
  (e) J. Ren, C. Pi, Y. Wu, X. Cui, Org. Lett. 11 (2019) 4067-4071; f) S. Huang, H. Li, X. Sun, et al., Org. Lett. 21 (2019) 5570-5574;
  (g) B. Wu, Z. Yang, H. Zhang, L. Wang, Cui X, Chem. Commun. 55 (2019) 4190-4193;
  (h) Z. Yang, Z. Song, L. Jie, L. Wang, X. Cui, Chem. Commun. 55 (2019) 6094-6097;
  (i) T. Yuan, C. Pi, C. You, et al., Chem. Commun. 55 (2019) 163-166;
  (k) T. Wan, S. Du, C. Pi, Y. Wang, R. Li, Y. Wu, X. Cui, ChemCatChem 11 (2019) 3791-3796;
  (l) S. Du, C. Pi, T. Wan, Y. Wu, X. Cui, Adv. Synth. Catal. 361 (2019) 1766-1770;
  (m) Z.H. Shen, C. Pi, X. Cui, Y. Wu, Chin. Chem. Lett. 30 (2019) 1374-1378.
1. [1]
  Jun Zhang , Zhiyao Zheng , Can Zhu . Stereochemical editing: Catalytic racemization of secondary alcohols and amines. Chinese Chemical Letters, 2024, 35(5): 109160-. doi: 10.1016/j.cclet.2023.109160
2. [2]
  Xinghao Cai , Chen Ma , Ying Kang , Yuqiang Ren , Xue Meng , Wei Lu , Shiming Fan , Shouxin Liu . Nickel-catalyzed C(sp²)–H alkynylation of free α-substituted benzylamines using a transient directing group. Chinese Chemical Letters, 2025, 36(10): 110901-. doi: 10.1016/j.cclet.2025.110901
3. [3]
  Jian Peng , Yue Jiang , Shuangyu Wu , Yanran Cheng , Jingyu Liang , Yixin Wang , Zhuo Li , Sijie Lin . A nonradical oxidation process initiated by Ti-peroxo complex showed high specificity toward the degradation of tetracycline antibiotics. Chinese Chemical Letters, 2024, 35(5): 108903-. doi: 10.1016/j.cclet.2023.108903
4. [4]
  Xin Li , Jia-Min Lu , Bo Li , Chen Zhao , Bei-Bei Yang , Li Li . Chiroptical sensing for remote chiral amines via a C–H activation reaction. Chinese Chemical Letters, 2025, 36(5): 110310-. doi: 10.1016/j.cclet.2024.110310
5. [5]
  Qi Li , Zi-Lu Wang , Yun-He Xu . Copper-catalyzed 1,4-silylcyanation of 1,3-enynes: A silyl radical-initiated approach for synthesis of difunctionalized allenes. Chinese Chemical Letters, 2025, 36(3): 109991-. doi: 10.1016/j.cclet.2024.109991
6. [6]
  Wen-Tao Ouyang , Jun Jiang , Yan-Fang Jiang , Ting Li , Yuan-Yuan Liu , Hong-Tao Ji , Li-Juan Ou , Wei-Min He . Sono-photocatalytic amination of quinoxalin-2(1H)-ones with aliphatic amines. Chinese Chemical Letters, 2024, 35(10): 110038-. doi: 10.1016/j.cclet.2024.110038
7. [7]
  Xiuhua Wang , Jianrong Steve Zhou . A dicationic nickel complex-catalyzed asymmetric synthesis of chiral benzylic amines: Evolution from reductive amination to borrowing hydrogen reaction. Chinese Chemical Letters, 2026, 37(2): 111148-. doi: 10.1016/j.cclet.2025.111148
8. [8]
  Yuan Zhang , Shenghao Gong , A.R. Mahammed Shaheer , Rong Cao , Tianfu Liu . Plasmon-enhanced photocatalytic oxidative coupling of amines in the air using a delicate Ag nanowire@NH₂-UiO-66 core-shell nanostructures. Chinese Chemical Letters, 2024, 35(4): 108587-. doi: 10.1016/j.cclet.2023.108587
9. [9]
  Nianhua Luo , Jiayi Jiang , Muhammad Suleman , Zhaowen Liu , Shuping Huang , Wei Xiao , Jie Wu , Jiapian Huang . Advances in radical Smiles rearrangement. Chinese Chemical Letters, 2026, 37(2): 111556-. doi: 10.1016/j.cclet.2025.111556
10. [10]
  Min-Hang Zhou , Jun Jiang , Wei-Min He . EDA-complexes-enabled photochemical synthesis of α-amino acids with imines and tetrabutylammonium oxalate. Chinese Chemical Letters, 2025, 36(1): 110446-. doi: 10.1016/j.cclet.2024.110446
11. [11]
  Jun Liu , Zhaoyu Feng , Renming Pan , Xiaolong Yu , Meijuan Zhou , Gang Zhao , Hongyu Wang . Enantioselective regulation to coronal polyheterocyclic compounds via phosphonium salt-catalyzed cycloadditions of azomethine imines with γ-butenolides. Chinese Chemical Letters, 2025, 36(8): 110647-. doi: 10.1016/j.cclet.2024.110647
12. [12]
  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
13. [13]
  Qiang Fang , Yingbo Lu , Jianying Huang , Cheng Zhang , Jing Wu , Shijun Li . An electrochemical immunosensor based on an antibody-ferrocene-functionalized covalent organic framework. Chinese Chemical Letters, 2026, 37(2): 111218-. doi: 10.1016/j.cclet.2025.111218
14. [14]
  Ping Wang , Tianbao Zhang , Zhenxing Li . Reconstruction mechanism of Cu surface in CO2 reduction process. Chinese Journal of Structural Chemistry, 2024, 43(8): 100328-100328. doi: 10.1016/j.cjsc.2024.100328
15. [15]
  Zonglin Li , Shihua Zou , Zining Wang , Georgeta Postole , Liang Hu , Hongying Zhao . Machine learning in electrochemical oxidation process: A mini-review. Chinese Chemical Letters, 2025, 36(8): 110526-. doi: 10.1016/j.cclet.2024.110526
16. [16]
  Lina Xie , Xiaohe Zhang , Xiaobo Wang , Zhen Zhang , Tianqi Nie , Jun Wu , Xiaojun Xu . Multifunctional GelMA hydrogel doped with spermidine-ferrocene polymeric nanoparticles for accelerative diabetic wound healing. Chinese Chemical Letters, 2025, 36(11): 110848-. doi: 10.1016/j.cclet.2025.110848
17. [17]
  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
18. [18]
  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
19. [19]
  Hong-Qiang Dong , Shang-Bo Yu , Shu-Meng Wang , Jia-Hao Zhao , Xu-Guan Bai , Shi-Xing Lei , Zhen-Nan Tian , Jia Tian , Kang-Da Zhang , Lu Wang , Zhan-Ting Li , Shigui Chen . Construction of radical halogen-bonded organic frameworks with enhanced magnetism and conductivity. Chinese Chemical Letters, 2025, 36(8): 110730-. doi: 10.1016/j.cclet.2024.110730
20. [20]
  Hui-Xian Jiang , Zhi-Tao Liu , Pei Xu , Xu Zhu . Synthetic application of oxalate salts for visible-light-induced radical transformations. Chinese Chemical Letters, 2025, 36(12): 111224-. doi: 10.1016/j.cclet.2025.111224

Get Citation

PDF

XML

Metrics

PDF Downloads(8)
Abstract views(1530)
HTML views(44)

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