Citation: Mojtaba Amini, Mojtaba Bagherzadeh, Sadegh Rostamnia. Efficient imidazolium salts for palladium-catalyzed Mizoroki-Heck and Suzuki-Miyaura cross-coupling reactions[J]. Chinese Chemical Letters, ;2013, 24(05): 433-436. shu

Efficient imidazolium salts for palladium-catalyzed Mizoroki-Heck and Suzuki-Miyaura cross-coupling reactions

a Department of Chemistry, Faculty of Science, University of Maragheh, Maragheh, P.
a Department of Chemistry, Faculty of Science, University of Maragheh, Maragheh, P. O. Box 55181-83111731, Iran;
b Chemistry Department, Sharif University of Technology, Tehran, P.
b Chemistry Department, Sharif University of Technology, Tehran, P. O. Box 11155-3615, Iran

Corresponding author: Mojtaba Amini, Mojtaba Bagherzadeh,
Received Date: 5 January 2013
Available Online: 8 March 2013

The system, Pd(OAc)₂/imidazolium salts (L₂), was found as an efficient catalyst in the Heck coupling reaction of olefins with aryl halides and Suzuki reactions of various aryl halides with aryl boronic acids under aerobic condition. This catalytic system demonstrates great tolerance to a wide range of groups on all substrates of aryl halides, alkenes and aryl boronic acids.
- Imidazolium salt,
- Heck coupling reaction,
- Suzuki coupling reaction,
- Pd(OAc)₂
1. [1]
  [1] R.F. Heck, Palladium Reagents in Organic Synthesis, Academic Press, London, 1985.
2. [2]
  [2] J. Tsuji, Palladium Reagents and Catalysts, John Wiley and Sons, Chichester, 1995.
3. [3]
  [3] X.F. Wu, H. Neumann, M. Beller, Palladium-catalyzed carbonylative coupling reactions of aryl iodides with hexamethyldisilane (HMDS) to benzoyl silanes, Tetrahedron Lett. 53 (2012) 582-584.
4. [4]
  [4] F. Diederich, P.J. Stang, Metal-Catalyzed Cross-Coupling Reactions, Wiley-VCH, Weinheim, 1998.
5. [5]
  [5] M. Amini, M. Bagherzadeh, Z. Moradi-Shoeili, D.M. Boghaei, Pd(OAc)₂ without added ligand as an active catalyst for Mizoroki-Heck reaction in aqueous media, RSC Adv. 2 (2012) 12091-12095.
6. [6]
  [6] P. Karthikeyan, P.N. Muskawar, S.A. Aswar, P.R. Bhagat, S.K. Sythana, Development of an efficient solvent free one-pot Heck reaction catalyzed by novel palladium (Ⅱ) complex-via green approach, J. Mol. Catal. A: Chem. 358 (2012) 112-120.
7. [7]
  [7] M. Bagherzadeh, M. Amini, A. Ellern, L.K. Woo, Palladium and copper complexes with oxygen-nitrogen mixed donors as efficient catalysts for the Heck reaction, Inorg. Chim. Acta 383 (2012) 46-51.
8. [8]
  [8] Q. Du, W. Zhang, H. Ma, et al., Immobilized palladium on surface-modified Fe₃O₄/SiO₂ nanoparticles: as a magnetically separable and stable recyclable high-performance catalyst for Suzuki and Heck cross-coupling reactions, Tetrahedron 68 (2012) 3577-3584.
9. [9]
  [9] W.A. Herrmann, N-heterocyclic carbenes: a new concept in organometallic catalysis, Angew. Chem. Int. Ed. 41 (2002) 1290-1309.
10. [10]
  [10] A.C. Hillier, G.A. Grasa, M.S. Viciu, et al., Catalytic cross-coupling reactions mediated by palladium/nucleophilic carbene systems, J. Organomet. Chem. 653 (2002) 69-82.
11. [11]
  [11] M.C. Jahnke, M. Hussain, F. Hupka, et al., Synthesis of pyrazine-bridged diimidazolium salts and their application in palladium catalyzed Heck-type coupling reactions, Tetrahedron 65 (2009) 909-913.
12. [12]
  [12] E. Peris, R.H. Crabtree, Recent homogeneous catalytic applications of chelate and pincer N-heterocyclic carbenes, Coord. Chem. Rev. 248 (2004) 2239-2246.
13. [13]
  [13] C.M. Crudden, D.P. Allen, Stability and reactivity of N-heterocyclic carbene complexes, Coord. Chem. Rev. 248 (2004) 2247-2273.
14. [14]
  [14] P. de Frémont, N. Marion, S.P. Nolan, Carbenes: synthesis, properties, and organometallic chemistry, Coord. Chem. Rev. 253 (2009) 862-892.
15. [15]
  [15] A.J. Arduengo, F. Davidson, H.V.R.J. Dias, et al., An air stable carbene and mixed carbene "dimers", J. Am. Chem. Soc. 119 (1997) 12742-12749.
16. [16]
  [16] A.J. Arduengo Ⅲ, R. Krafczyk, R. Schmutzler, Imidazolylidenes, imidazolinylidenes and imidazolidines, Tetrahedron 55 (1999) 14523-14534.
1. [1]
  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
2. [2]
  Xuhui Fan , Fan Wang , Mengjiao Li , Faiza Meharban , Yaying Li , Yuanyuan Cui , Xiaopeng Li , Jingsan Xu , Qi Xiao , Wei Luo . Visible light excitation on CuPd/TiN with enhanced chemisorption for catalyzing Heck reaction. Chinese Chemical Letters, 2025, 36(1): 110299-. doi: 10.1016/j.cclet.2024.110299
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]
  Guan-Nan Xing , Di-Ye Wei , Hua Zhang , Zhong-Qun Tian , Jian-Feng Li . Pd-based nanocatalysts for oxygen reduction reaction: Preparation, performance, and in-situ characterization. Chinese Journal of Structural Chemistry, 2023, 42(11): 100021-100021. doi: 10.1016/j.cjsc.2023.100021
5. [5]
  Min Song , Qian Zhang , Tao Shen , Guanyu Luo , Deli Wang . Surface reconstruction enabled o-PdTe@Pd core-shell electrocatalyst for efficient oxygen reduction reaction. Chinese Chemical Letters, 2024, 35(8): 109083-. doi: 10.1016/j.cclet.2023.109083
6. [6]
  Xinlong Han , Huiying Zeng , Chao-Jun Li . Trifluoromethylative homo-coupling of carbonyl compounds. Chinese Chemical Letters, 2025, 36(1): 109817-. doi: 10.1016/j.cclet.2024.109817
7. [7]
  Yuexiang Liu , Xiangqiao Yang , Tong Lin , Guantian Yang , Xiaoyong Xu , Bubing Zeng , Zhong Li , Weiping Zhu , Xuhong Qian . Efficient continuous synthesis of 2-[3-(trifluoromethyl)phenyl]malonic acid, a key intermediate of Triflumezopyrim, coupling with esterification-condensation-hydrolysis. Chinese Chemical Letters, 2025, 36(1): 109747-. doi: 10.1016/j.cclet.2024.109747
8. [8]
  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
9. [9]
  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
10. [10]
  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
11. [11]
  Qijun Tang , Wenguang Tu , Yong Zhou , Zhigang Zou . High efficiency and selectivity catalyst for photocatalytic oxidative coupling of methane. Chinese Journal of Structural Chemistry, 2023, 42(12): 100170-100170. doi: 10.1016/j.cjsc.2023.100170
12. [12]
  Kongchuan Wu , Dandan Lu , Jianbin Lin , Ting-Bin Wen , Wei Hao , Kai Tan , Hui-Jun Zhang . Elucidating ligand effects in rhodium(Ⅲ)-catalyzed arene–alkene coupling reactions. Chinese Chemical Letters, 2024, 35(5): 108906-. doi: 10.1016/j.cclet.2023.108906
13. [13]
  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
14. [14]
  Xin Huang , Yi Zhao , Wanzhen Liang . Vibronic coupling effect on intersystem crossing rates of TADF emitters. Chinese Journal of Structural Chemistry, 2024, 43(6): 100278-100278. doi: 10.1016/j.cjsc.2024.100278
15. [15]
  Jian Ji , Jie Yan , Honggen Peng . Modulation of dinuclear site by orbital coupling to boost catalytic performance. Chinese Journal of Structural Chemistry, 2024, 43(8): 100360-100360. doi: 10.1016/j.cjsc.2024.100360
16. [16]
  Yuehai Zhi , Chen Gu , Huachao Ji , Kang Chen , Wenqi Gao , Jianmei Chen , Dafeng Yan . The advanced development of innovative photocatalytic coupling strategies for hydrogen production. Chinese Chemical Letters, 2025, 36(1): 110234-. doi: 10.1016/j.cclet.2024.110234
17. [17]
  Haojie Duan , Hejingying Niu , Lina Gan , Xiaodi Duan , Shuo Shi , Li Li . Reinterpret the heterogeneous reaction of α-Fe₂O₃ and NO₂ with 2D-COS: The role of SDS, UV and SO₂. Chinese Chemical Letters, 2024, 35(6): 109038-. doi: 10.1016/j.cclet.2023.109038
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(0)
Abstract views(592)
HTML views(15)

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