Citation: Bai Yali, Li Xiaowei, Xiao Xuedong, Liu Jiaqi, Yang Junjuan, Wang Junwen. Synthesis of Imidazolium Precursors for the Hydroxyl-Group-Modified N-Heterocyclic Carbenes and Applications of the in situ Generated Carbene Ligands in Suzuki-Miyaura and Sonogashira Coupling Reactions[J]. Chinese Journal of Organic Chemistry, ;2017, 37(5): 1258-1265. doi: 10.6023/cjoc201610039 shu

Synthesis of Imidazolium Precursors for the Hydroxyl-Group-Modified N-Heterocyclic Carbenes and Applications of the in situ Generated Carbene Ligands in Suzuki-Miyaura and Sonogashira Coupling Reactions

Bai Yali ^a ,
Li Xiaowei ^b ,
Xiao Xuedong ^a ,
Liu Jiaqi ^a ,
Yang Junjuan ^a ,
Wang Junwen ^a,*,,

a.
Department of Chemistry, Shanxi Normal University, Linfen 041000
b.
Inner Mongolia Datang International Renewable Resources Development Co. Ltd., Hohhot 010000

Corresponding author: Wang Junwen, wangjunwen2013@126.com
Received Date: 22 October 2016
Revised Date: 6 December 2016

Fund Project: Project supported by the Basic Research Project of Shanxi Province of China 2015011029and the Shanxi Province Education Innovation Project for Postgraduate 2015BY38the Undergraduate Innovative Experiment Program of Shanxi Normal University SD2014CXXM-36

Figures(4)

Four imidazolium precursors for the N-heterocyclic carbenes (NHCs) with a hydroxyl functionalized four-mem-bered heterocyclic side arm were synthesized and characterized by IR, XRD and NMR spectroscopies. The corresponding NHC ligands thus generated in situ from these imidazolium precursors in the presence of base such as KOH, together with PdCl₂(CH₃CN)₂, exhibited excellent catalytic activity in Suzuki-Miyaura cross-coupling reactions for the synthesis of a range of biaryl compounds. The reactions could be conducted in the mixed solvent of tert-butyl alcohol/water (V:V=1:1) at room temperature with the advantages of mild conditions, high efficiency as well as environmental friendliness. In addition, although in minor amount, the mixed catalyst system containing imidazolium salts, PdCl₂(CH₃CN)₂ (0.1%) and CuI (1%) exhibited excellent catalytic activity in Sonogashira coupling reaction. In particular, the combination system of PdCl₂/imidazolium salt 3b has been shown to be higher catalytically active for both coupling reactions.
- hydroxyl group,
- N-heterocyclic carbene,
- palladium,
- Suzuki-Miyaura cross-coupling,
- Sonogashira cross-coupling
1. [1]
  Arduengo, A. J.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361. doi: 10.1021/ja00001a054
2. [2]
  Qu, M. N.; He, J. M. Chin. J. Org. Chem. 2011, 31, 1388 (in Chinese).
3. [3]
  Tang, Y.; Yang, F. F.; Nie, S. P.; Wang, L.; Luo, Z. B.; Lu, H. F. Chin. J. Org. Chem. 2015, 35, 705 (in Chinese).
4. [4]
  Zhang, D.; Zi, G. F. Chem. Soc. Rev. 2015, 44, 1898. doi: 10.1039/C4CS00441H
5. [5]
  Barroso, S.; de Aguiar, S. R. M. M.; Munhá, R. F.; Martins, A. M. J. Organomet. Chem. 2014, 760, 60. doi: 10.1016/j.jorganchem.2013.11.041
6. [6]
  Zhao, N.; Hou, G. H.; Deng, X. B.; Zi, G. F.; Walter, M. D. Dalton Trans. 2014, 43, 8261. doi: 10.1039/C4DT00510D
7. [7]
  Hameury, S.; de Frémont, P.; Breuil, P. A. R.; Olivier-Bourbigou, H.; Braunstein, P. Inorg. Chem., 2014, 53, 5189. doi: 10.1021/ic500349t
8. [8]
  Ohmiya, H.; Zhang, H.; Shibata, S.; Harada, A.; Sawamura, M. Angew. Chem. 2016, 128, 4855. doi: 10.1002/ange.201600619
9. [9]
10. [10]
  Fortman, G. C.; Nolan, S. P. Chem. Soc. Rev. 2011, 40, 5151. doi: 10.1039/c1cs15088j
11. [11]
  Levin, E.; Ivry, E.; Diesendruck, C. E.; Lemcoff, N. G. Chem. Rev. 2015, 115, 4607. doi: 10.1021/cr400640e
12. [12]
  Schmid, T. E.; Jones, D. C.; Songis, O.; Diebolt, O.; Furst, M. R. L.; Slawin, A. M. Z.; Cazin, C. S. J. Dalton Trans. 2013, 42, 7345. doi: 10.1039/c2dt32858e
13. [13]
  Neumann, K. T.; Laursen, S. R.; Lindhardt, A. T.; Bang-Andersen, B.; Skrydstrup, T. Org. Lett. 2014, 16, 2216. doi: 10.1021/ol5007289
14. [14]
  Caddick, S.; Cloke, F. G. N.; Clentsmith, G. K. B.; Hitchcock, P. B.; McKerrecher, D.; Titcomb, L. R.; Williams, M. R. V. J. Organomet. Chem. 2001, 617, 635.
15. [15]
  Burkhard, J. A.; Wagner, B.; Fischer, H.; Schuler, F.; Müller, K.; Carreira, E. M. Angew. Chem., Int. Ed. 2010, 49, 3524. doi: 10.1002/anie.200907108
16. [16]
  Burkhard, J. A.; Guérot, C.; Knust, H.; Rogers-Evans, M.; Carreira, E. M. Org. Lett. 2010, 12, 1944. doi: 10.1021/ol1003302
17. [17]
  Burkhard, J.; Carreira, E. M. Org. Lett. 2008, 10, 3525. doi: 10.1021/ol801293f
18. [18]
  Wuitschik, G.; Rogers-Evans, M.; Buckl, A.; Bernasconi, M.; Märki, M.; Godel, T.; Fischer, H.; Wagner, B.; Parrilla, I.; Schuler, F.; Schneider, J.; Alker, A.; Schweizer, W. B.; Müller, K.; Carreira, E. M. Angew. Chem. 2008, 120, 4588. doi: 10.1002/(ISSN)1521-3757
19. [19]
  Wang, J. W.; Li, Q. S.; Xu, F. B.; Song, H. B.; Zhang, Z. Z. Eur. J. Org. Chem. 2006, 1310.
20. [20]
  Yu, L.; Han, Z. Mater. Lett. 2016, 184, 312. doi: 10.1016/j.matlet.2016.08.056
21. [21]
  Al-Amin, M.; Akimoto, M.; Tameno, T.; Ohki, Y.; Takahashi, N.; Hoshiya, N.; Shuto, S.; Arisawa, M. Green Chem. 2013, 15, 1142. doi: 10.1039/c3gc00063j
22. [22]
  Ma, H. C.; Cao, W.; Bao, Z. K.; Lei, Z. Q. Catal. Sci. Technol. 2012, 2, 2291. doi: 10.1039/c2cy20126g
23. [23]
  Zhao, X. H.; Zhao, Y. Y.; Zhang, J.; Li, X. Appl. Organomet. Chem. 2015, 29, 840. doi: 10.1002/aoc.3391
24. [24]
  Yadav, R. R.; Vishwakarma, R. A.; Bharate, S. B. Tetrahedron Lett. 2012, 53, 5958. doi: 10.1016/j.tetlet.2012.08.121
25. [25]
  Hassine, A.; Sebti, S.; Solhy, A.; Zahouily, M.; Len, C.; Hedhili, M. N.; Fihri, A. Appl. Catal., A 2013, 450, 13. doi: 10.1016/j.apcata.2012.09.046
26. [26]
  Siamaki, A. R.; Lin, Y.; Woodberry, K.; Connell, J. W.; Gupton, B. F. J. Mater. Chem. A 2013, 1, 12909.
27. [27]
  Iranpoor, N.; Firouzabadi, H.; Motevalli, S.; Rajabi, K. Aust. J. Chem. 2015, 68, 926. doi: 10.1071/CH14332
28. [28]
  Zhang, G. P.; Li, P. H. Chin. J. Org. Chem. 2010, 30, 117 (in Chinese).
29. [29]
  Elumalai, V.; Bjørsvik, H. R. Tetrahedron Lett. 2016, 57, 1224. doi: 10.1016/j.tetlet.2016.02.007
30. [30]
  Wang, X.; Wang, Z. H.; Wu, Y.; Luo, Y. L.; Zhang, G. F.; Jian, Y. J.; Sun, H. M.; Zhang, W. Q.; Gao, Z. W. Appl. Organomet. Chem. 2016, 30, 831. doi: 10.1002/aoc.v30.10
31. [31]
  Sagadevan, A.; Hwang, K. C. Adv. Synth. Catal. 2012, 354, 3421. doi: 10.1002/adsc.v354.18
1. [1]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
2. [2]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
3. [3]
  Qiang Zhang , Yuanbiao Huang , Rong Cao . Imidazolium-Based Materials for CO₂ Electroreduction. Acta Physico-Chimica Sinica, 2024, 40(4): 2306040-0. doi: 10.3866/PKU.WHXB202306040
4. [4]
  Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
5. [5]
  Jiaqi AN , Yunle LIU , Jianxuan SHANG , Yan GUO , Ce LIU , Fanlong ZENG , Anyang LI , Wenyuan WANG . Reactivity of extremely bulky silylaminogermylene chloride and bonding analysis of a cubic tetragermylene. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1511-1518. doi: 10.11862/CJIC.20240072
6. [6]
  Lili Jiang , Shaoyu Zheng , Xuejiao Liu , Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
7. [7]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
8. [8]
  Xiyuan Zhang , Rui Dong , Yang Yang , Jiapeng Ding , Zhiwei Miao . Palladium-Catalyzed Tandem Cyclization of 4-Vinylbenzoxazinone and Indene-2-carbaldehyde: A Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(9): 361-367. doi: 10.12461/PKU.DXHX202410062
9. [9]
  Xinyu Zhu , Meili Pang . Application of Functional Group Addition Strategy in Organic Synthesis. University Chemistry, 2024, 39(3): 218-230. doi: 10.3866/PKU.DXHX202308106
10. [10]
  Wen Jiang , Jieli Lin , Zhongshu Li . 低配位含磷官能团的研究进展. University Chemistry, 2025, 40(8): 138-151. doi: 10.12461/PKU.DXHX202409144
11. [11]
  Yuanyuan Ping , Wangqing Kong . 光催化碳氢键官能团化合成1-苯基-1,2-乙二醇. University Chemistry, 2025, 40(6): 238-247. doi: 10.12461/PKU.DXHX202408092
12. [12]
  Zhiming Feng , Lili Wu , Chengming Wang . Doubly Oxidized Carbene. University Chemistry, 2025, 40(9): 326-331. doi: 10.12461/PKU.DXHX202411008
13. [13]
  Ruizhi Duan , Xiaomei Wang , Panwang Zhou , Yang Liu , Can Li . The role of hydroxyl species in the alkaline hydrogen evolution reaction over transition metal surfaces. Acta Physico-Chimica Sinica, 2025, 41(9): 100111-0. doi: 10.1016/j.actphy.2025.100111
14. [14]
  Jie ZHAO , Huili ZHANG , Xiaoqing LU , Zhaojie WANG . Theoretical calculations of CO₂ capture and separation by functional groups modified 2D covalent organic framework. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 275-283. doi: 10.11862/CJIC.20240213
15. [15]
  Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
16. [16]
  Zhuoyan Lv , Yangming Ding , Leilei Kang , Lin Li , Xiao Yan Liu , Aiqin Wang , Tao Zhang . Light-Enhanced Direct Epoxidation of Propylene by Molecular Oxygen over CuO_x/TiO₂ Catalyst. Acta Physico-Chimica Sinica, 2025, 41(4): 2408015-0. doi: 10.3866/PKU.WHXB202408015
17. [17]
  Jichao XU , Ming HU , Xichang CHEN , Chunhui WANG , Leichen WANG , Lingyi ZHOU , Xing HE , Xiamin CHENG , Su JING . Construction and hydrogen peroxide-activated chemodynamic activity of ferrocene?benzoselenadiazole conjugate. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1495-1504. doi: 10.11862/CJIC.20250144
18. [18]
  Shiqian WEI , Xinyu TIAN , Hong LIU , Maoxia CHEN , Fan TANG , Qiang FAN , Weifeng FAN , Yu HU . Oxygen reduction reaction/oxygen evolution reaction catalytic performances of different active sites on nitrogen-doped graphene loaded with iron single atoms. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1776-1788. doi: 10.11862/CJIC.20250102
19. [19]
  Weihan Zhang , Menglu Wang , Ankang Jia , Wei Deng , Shuxing Bai . Surface Sulfur Species Influence Hydrogenation Performance of Palladium-Sulfur Nanosheets. Acta Physico-Chimica Sinica, 2024, 40(11): 2309043-0. doi: 10.3866/PKU.WHXB202309043
20. [20]
  Yi Yang , Xin Zhou , Miaoli Gu , Bei Cheng , Zhen Wu , Jianjun Zhang . Femtosecond transient absorption spectroscopy investigation on ultrafast electron transfer in S-scheme ZnO/CdIn₂S₄ photocatalyst for H₂O₂ production and benzylamine oxidation. Acta Physico-Chimica Sinica, 2025, 41(6): 100064-0. doi: 10.1016/j.actphy.2025.100064

Get Citation

PDF

XML

Metrics

PDF Downloads(8)
Abstract views(1410)
HTML views(240)

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