Citation: Meng-Yao ZHANG, Hui-Xin ZHANG, Ying-Ying ZHANG, Yong-Fei ZENG, Gui-Yan LIU. Synthesis, Crystal Structure and Catalytic Activity of a Dichlorobridged Dimeric Cu(Ⅱ) Complex Bearing 2,2΄-(1H-1,2,4-triazole-1,3-diyl)dipyridine Ligands[J]. Chinese Journal of Structural Chemistry, ;2020, 39(9): 1723-1728. doi: 10.14102/j.cnki.0254-5861.2011-2683 shu

Synthesis, Crystal Structure and Catalytic Activity of a Dichlorobridged Dimeric Cu(Ⅱ) Complex Bearing 2,2΄-(1H-1,2,4-triazole-1,3-diyl)dipyridine Ligands

Tianjin Key Laboratory of Structure and Performance for Functional Molecules; Key Laboratory of Inorganic-organic Hybrid Functional Material Chemistry (Tianjin Normal University); Ministry of Education; College of Chemistry, Tianjin Normal University, Tianjin 300387, China

Corresponding author: Yong-Fei ZENG, yfzeng@nankai.edu.cn Gui-Yan LIU, guiyanliu2013@163.com
Received Date: 2 December 2019
Accepted Date: 4 June 2020

Fund Project: the Natural Science Foundation of Tianjin 16JCYBJC19700the National Natural Science Foundation of China 21771138

Figures(3)

A new dichlorobridged dimeric Cu(Ⅱ) complex bearing 2,2΄-(1H-1,2,4-triazole-1,3-diyl)dipyridine ligands has been synthesized. Its structure has been characterized by X-ray single-crystal diffraction. New Cu(Ⅱ) complex crystallizes in triclinic system, space group P\begin{document}$ \overline 1 $\end{document} with a = 7.5080(11), b = 10.5954(13), c = 12.4383(15) Å, α = 76.320(10), β = 74.826(11), γ = 70.517(12)°, V = 888.1(2) Å³, Z = 2, ρ_calc = 1.784 g/cm³, μ = 1.987 mm^–1, F(000) = 474, the final R = 0.1010 and wR = 0.1520 for 5688 observed reflections (I > 2σ(I)), R(all data) = 0.1872, wR(all data) = 0.1806, completeness to theta of 25.010 is 100.0% and GOF = 1.060. Furthermore, the dichlorobridged dimeric Cu(Ⅱ) complex showed high catalytic activity for the Ullmann coupling reaction of (hetero)aryl chlorides with various N(H)-heterocycles.
- Cu(Ⅱ) complex,
- Ullmann coupling reaction,
- (hetero)aryl chlorides,
- N(H)-heterocycles
1. [1]
  Craig, P. N. In Comprehensive Medicinal Chemistry. Drayton, C. J., Ed.; Pergamon Press: New York 1991, Vol. 8.
2. [2]
  Horton, D. A.; Bourne, G. T.; Smythe, M. L. The combinatorial synthesis of bicyclic privileged structures or privileged substructures. Chem. Rev. 2003, 103, 893–930. doi: 10.1021/cr020033s
3. [3]
  Evano, G.; Blanchard, N.; Toumi, M. Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis. Chem. Rev. 2008, 108, 3054–3131. doi: 10.1021/cr8002505
4. [4]
  Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Aryl-aryl bond formation one century after the discovery of the Ullmann reaction. Chem. Rev. 2002, 102, 1359–1470. doi: 10.1021/cr000664r
5. [5]
  Ley, S. V.; Thomas, A. W. Modern synthetic methods for copper-mediated C(aryl)-O, C(aryl)-N, and C(aryl)-S bond formation. Angew. Chem., Int. Ed. 2003, 42, 5400–5449. doi: 10.1002/anie.200300594
6. [6]
  Sambiagio, C.; Marsden, S. P.; Blacker, A. J.; McGowan, P. C. Copper catalysed Ullmann type chemistry: from mechanistic aspects to modern development. Chem. Soc. Rev. 2014, 43, 3525–3550. doi: 10.1039/C3CS60289C
7. [7]
  Bhunia, S.; Pawar, G. G.; Kumar, S. V.; Jiang, Y. W.; Ma, D. W. Selected copper-based reactions for C–N, C–O, C–S, and C–C bond formation. Angew. Chem., Int. Ed. 2017, 56, 16136–16179. doi: 10.1002/anie.201701690
8. [8]
  Klapars, A.; Huang, X. H.; Buchwald, S. L. A general and efficient copper catalyst for the amidation of aryl halides. J. Am. Chem. Soc. 2002, 124, 7421–7428. doi: 10.1021/ja0260465
9. [9]
  Pawar, G. G.; Wu, H. B.; De, S.; Ma, D. W. Copper(Ⅰ) oxide/N, N΄-bis[(2-furyl)methyl]oxalamide-catalyzed coupling of (hetero)aryl halides and nitrogen heterocycles at low catalytic loading. Adv. Synth. Catal. 2017, 359, 1631–1636. doi: 10.1002/adsc.201700026
10. [10]
  Altman, R. A.; Koval, E. D.; Buchwald, S. L. Copper-catalyzed N-arylation of imidazoles and benzimidazoles. J. Org. Chem. 2007, 72, 6190–6199. doi: 10.1021/jo070807a
11. [11]
  Zhao, Y. Y.; Wang, X. Y.; Kodama, K.; Hirose, T. Copper-catalyzed coupling reactions of aryl halides and phenols by 4,4'-dimethoxy-2,2'-bipyridine and 4,7-dimethoxy-1,10-phenanthroline. Chem. Select. 2018, 3, 12620–12624.
12. [12]
  Yuan, Q. L.; Ma, D. W. A one-pot coupling/hydrolysis/condensation process to pyrrolo[1,2-a]quinoxaline. J. Org. Chem. 2008, 73, 5159–5162. doi: 10.1021/jo8008098
13. [13]
  Tang, J. M.; Xu, B. Q.; Mao, X.; Yang, H. Y.; Wang, X. X.; Lv, X. One-pot synthesis of pyrrolo[3,2,1-kl]phenothiazines through copper-catalyzed tandem coupling/double cyclization reaction. J. Org. Chem. 2015, 80, 11108–11114. doi: 10.1021/acs.joc.5b01745
14. [14]
  Shafir, A.; Buchwald, S. L. Highly selective room-temperature copper-catalyzed C-N coupling reactions. J. Am. Chem. Soc. 2006, 128, 8742–8743. doi: 10.1021/ja063063b
15. [15]
  Liu, L. B.; Frohn, M.; Xi, N.; Dominguez, C.; Hungate, R.; Reider, P. J. A soluble base for the copper-catalyzed imidazole N-arylations with aryl halides. J. Org. Chem. 2005, 70, 10135–10138. doi: 10.1021/jo051640t
16. [16]
  Ueda, S.; Buchwald, S. L. Catalyst-controlled chemoselective arylation of 2-aminobenzimidazoles. Angew. Chem., Int. Ed. 2012, 51, 10364–10367. doi: 10.1002/anie.201204710
17. [17]
  Cristau, H. J.; Cellier, P. P.; Spindler, J. F.; Taillefer, M. Highly efficient and mild copper-catalyzed N- and C-arylations with aryl bromides and iodides. Chem. Eur. J. 2004, 10, 5607–5622. doi: 10.1002/chem.200400582
18. [18]
  Enguehard, C.; Allouchi, H.; Gueifﬁer, A.; Buchwald, S. L. Easy access to novel substituted 6-aminoimidazo[1,2-a]pyridines using palladium- and copper-catalyzed aminations. J. Org. Chem. 2003, 68, 4367–4370. doi: 10.1021/jo0341463
19. [19]
  Zhang, C.; Huang, B.; Bao, A. Q.; Li, X.; Guo, S. N.; Zhang, J. Q.; Xu, J. Z.; Zhang, R. H.; Cui, D. M. Copper-catalyzed arylation of biguanide derivatives via C–N cross-coupling reactions. Org. Biomol. Chem. 2015, 13, 11432–11437. doi: 10.1039/C5OB01258A
20. [20]
  Suresh, P.; Pitchumani, K. Per-6-amino-β-cyclodextrin as an efficient supramolecular ligand and host for Cu(Ⅰ)-catalyzed N-arylation of imidazole with aryl bromides. J. Org. Chem. 2008, 73, 9121–9124. doi: 10.1021/jo801811w
21. [21]
  Liu, G. Y.; Xu, Y.; Liu, C. X. Synthesis, structural characterization and catalytic activity of copper(Ⅰ) complexes with triphenylphosphine and pyridine derivatives. Chin. J. Struct. Chem. 2016, 35, 740–746.
22. [22]
  Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. OLEX2: a complete structure solution, refinement and analysis program. J Appl Crystallogr. 2009, 42, 339–341. doi: 10.1107/S0021889808042726
23. [23]
  Sheldrick, G. M. SHELXT-integrated space-group and crystal-structure determination. Acta Crystallographica. Section A. Foundations and Advances 2015, 71, 3–8. doi: 10.1107/S2053273314026370
24. [24]
  Sheldrick, G. M. Crystal structure refinement with SHELXL. Acta Crystallographica. Section C, Structural Chemistry 2015, 71, 3–8. doi: 10.1107/S2053229614024218
1. [1]
  Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007
2. [2]
  Mengli Xu , Zhenmin Xu , Zhenfeng Bian . Achieving Ullmann coupling reaction via photothermal synergy with ultrafine Pd nanoclusters supported on mesoporous TiO2. Chinese Journal of Structural Chemistry, 2024, 43(7): 100305-100305. doi: 10.1016/j.cjsc.2024.100305
3. [3]
  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
4. [4]
  Lu Dai , Yuxin Ren , Shuang Li , Meidi Wang , Chentao Hu , Ya-Pan Wu , Guangtong Hai , Dong-Sheng Li . Room-temperature synthesis of Co(OH)₂/Mo₂TiC₂T_x hetero-nanosheets with interfacial coupling for enhanced oxygen evolution reaction. Chinese Chemical Letters, 2025, 36(4): 109774-. doi: 10.1016/j.cclet.2024.109774
5. [5]
  Wenjuan Jin , Zelong Chen , Yi Wang , Jiaxuan Li , Jiahui Li , Yuxin Pei , Zhichao Pei . Nano metal-photosensitizer based on Aza-BODIPY-Cu complex for CDT-enhanced dual phototherapy. Chinese Chemical Letters, 2024, 35(7): 109328-. doi: 10.1016/j.cclet.2023.109328
6. [6]
  Junxin Li , Chao Chen , Yuzhen Dong , Jian Lv , Jun-Mei Peng , Yuan-Ye Jiang , Daoshan Yang . Ligand-promoted reductive coupling between aryl iodides and cyclic sulfonium salts by nickel catalysis. Chinese Chemical Letters, 2024, 35(11): 109732-. doi: 10.1016/j.cclet.2024.109732
7. [7]
  Bowen Wang , Longwu Sun , Qianqian Cao , Xinzhi Li , Jianai Chen , Shizhao Wang , Miaolin Ke , Fener Chen . Cu-catalyzed three-component CSP coupling for the synthesis of trisubstituted allenyl phosphorothioates. Chinese Chemical Letters, 2024, 35(12): 109617-. doi: 10.1016/j.cclet.2024.109617
8. [8]
  Ruike Hu , Kangmin Wang , Junxiang Liu , Jingxian Zhang , Guoliang Yang , Liqiu Wan , Bijin Li . Extended π-conjugated systems by external ligand-assisted C−H olefination of heterocycles: Facile access to single-molecular white-light-emitting and NIR fluorescence materials. Chinese Chemical Letters, 2025, 36(4): 110113-. doi: 10.1016/j.cclet.2024.110113
9. [9]
  Shengkai Li , Yuqin Zou , Chen Chen , Shuangyin Wang , Zhao-Qing Liu . Defect engineered electrocatalysts for C–N coupling reactions toward urea synthesis. Chinese Chemical Letters, 2024, 35(8): 109147-. doi: 10.1016/j.cclet.2023.109147
10. [10]
  Pengfei Zhang , Qingxue Ma , Zhiwei Jiang , Xiaohua Xu , Zhong Jin . Transition-metal-catalyzed remote meta-C—H alkylation and alkynylation of aryl sulfonic acids enabled by an indolyl template. Chinese Chemical Letters, 2024, 35(8): 109361-. doi: 10.1016/j.cclet.2023.109361
11. [11]
  Jinpeng Du , Junlin Chen , Yulong Shan , Tongliang Zhang , Yu Sun , Zhongqi Liu , Xiaoyan Shi , Wenpo Shan , Yunbo Yu , Hong He . Insight into the effects of C₃H₆ on fresh and hydrothermally aged Cu-SSZ-39 catalysts. Chinese Chemical Letters, 2025, 36(3): 110019-. doi: 10.1016/j.cclet.2024.110019
12. [12]
  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
13. [13]
  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
14. [14]
  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
15. [15]
  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
16. [16]
  Jialin Cai , Yizhe Chen , Ruiwen Zhang , Cheng Yuan , Zeyu Jin , Yongting Chen , Shiming Zhang , Jiujun Zhang . Interfacial Pt-N coordination for promoting oxygen reduction reaction. Chinese Chemical Letters, 2025, 36(2): 110255-. doi: 10.1016/j.cclet.2024.110255
17. [17]
  Yan Guo , Hongtao Bian , Le Yu , Jiani Ma , Yu Fang . Photochemical reaction mechanism of benzophenone protected guanosine at N7 position. Chinese Chemical Letters, 2025, 36(3): 109971-. doi: 10.1016/j.cclet.2024.109971
18. [18]
  Qinyu Zhao , Yunchao Zhao , Songjing Zhong , Zhaoyang Yue , Zhuoheng Jiang , Shaobo Wang , Quanhong Hu , Shuncheng Yao , Kaikai Wen , Linlin Li . Urchin-like piezoelectric ZnSnO₃/Cu₃P p-n heterojunction for enhanced cancer sonodynamic therapy. Chinese Chemical Letters, 2024, 35(12): 109644-. doi: 10.1016/j.cclet.2024.109644
19. [19]
  Yuemin Chen , Yunqi Wu , Guoao Wang , Feihu Cui , Haitao Tang , Yingming Pan . Electricity-driven enantioselective cross-dehydrogenative coupling of two C(sp³)-H bonds enabled by organocatalysis. Chinese Chemical Letters, 2024, 35(9): 109445-. doi: 10.1016/j.cclet.2023.109445
20. [20]
  Fahui Xiang , Lu Li , Zhen Yuan , Wuji Wei , Xiaoqing Zheng , Shimin Chen , Yisi Yang , Liangji Chen , Zizhu Yao , Jianwei Fu , Zhangjing Zhang , Shengchang Xiang . Enhanced C₂H₂/CO₂ separation in tetranuclear Cu(Ⅱ) cluster-based metal-organic frameworks by adjusting divider length of pore space partition. Chinese Chemical Letters, 2025, 36(3): 109672-. doi: 10.1016/j.cclet.2024.109672

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(294)
HTML views(2)

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