Citation: Da Yang, Dongliang Wang, Huan Liu, Xiaoli Zhao, Yong Lu, Shijun Lai, Ye Liu. Ionic palladium complex as an efficient and recyclable catalyst for the carbonylative Sonogashira reaction[J]. Chinese Journal of Catalysis, ;2016, 37(3): 405-411. doi: 10.1016/S1872-2067(15)61022-1 shu

Ionic palladium complex as an efficient and recyclable catalyst for the carbonylative Sonogashira reaction

1.
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China

Corresponding author: Shijun Lai, Ye Liu,
Received Date: 2 November 2015
Available Online: 23 November 2015
Fund Project: 国家自然科学基金(21473058,21273077). (21473058,21273077)

The neutral palladium(II) complex bis-[1-(5'-diphenylphosphinothiazol-2'-yl)-imidazolyl] dichloropalladium(II) (1A) ligated by thiazolylimidazolyl-based phosphine (L1) in which thiazolylimidazolyl acted as an S-and N-donor provider with weak coordinating nature, and the ionic complex bis-[1-(5'-diphenylphosphinothiazol-2'-yl)-3-methylimidazolium] dichloropalladium(II) trifluoromethanesulfonate (2A) ligated by thiazolylimidazolium-based phosphine (L2) after quaternization of L1 using methyl trifluoromethanesulphonate were synthesized. It was found that the introduced positive charges and strong electron-withdrawing effect in 2A not only led to changes in the configuration and structural stability of the complex, but also lowered its catalytic performance in carbonylative Sonogashira reactions. These effects reveal the important role of the N-donor in 1A. In addition, as an ionic palladium complex, 2A combined with the room-temperature ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate could be recycled eight times as the catalyst in carbonylative Sonogashira reactions without detectable metal leaching.
- Ionic phosphine ligand,
- Palladium complex,
- Carbonylative Sonogashira reaction,
- Ionic liquid
1. [1]
  [1] A. S. Karpov, E. Merkul, F. Rominger, T. J. J. Müller, Angew. Chem. Int. Ed., 2005, 44, 6951-6956.
2. [2]
  [2] C. J. Forsyth, J. Y. Xu, S. T. Nguyen, I. A. Samdal, L. R. Briggs, T. Rundberget, M. Sandvik, C. O. Miles, J. Am. Chem. Soc., 2006, 128, 15114-15116
3. [3]
  [3] L. F. Tietze, R. R. Singidi, K. M. Gericke, H. Bockemeier, H. Laatsch, Eur. J. Org. Chem., 2007, 5875-5878.
4. [4]
  [4] Z. L. Li, J. H. Liu, Z. W. Huang, Y. Yang, C. G. Xia, F. W. Li, ACS Catal., 2013, 3, 839-845.
5. [5]
  [5] D. A. Alonso, C. Nájera, M. C. Pacheco, J. Org. Chem., 2004, 69, 1615-1619.
6. [6]
  [6] B. M. Wang, M. Bonin, L. Micouin, J. Org. Chem., 2005, 70, 6126-6128.
7. [7]
  [7] L. Chen, C. J. Li, Org. Lett., 2004, 6, 3151-3153.
8. [8]
  [8] K. Y. Lee, M. J. Lee, J. N. Kim, Tetrahedron, 2005, 61, 8705-8710.
9. [9]
  [9] S. J. Yim, C. H. Kwon, D. K. An, Tetrahedron Lett., 2007, 48, 5393-5395.
10. [10]
  [10] T. Kobayashi, M. Tanaka, J. Chem. Soc., Chem. Commun., 1981, 333-334.
11. [11]
  [11] X. F. Wu, H. Neumann, M. Beller, Chem. Soc. Rev., 2011, 40, 4986-5009.
12. [12]
  [12] C. H. Bai, S. P. Jian, X. F. Yao, Y. W. Li, Catal. Sci. Technol., 2014, 4, 3261-3267.
13. [13]
  [13] Md. T. Rahman, T. Fukuyama, N. Kamata, M. Sato, I. Ryu, Chem. Commun., 2006, 2236-2238.
14. [14]
  [14] W. Y. Hao, J. C. Sha, S. R. Sheng, M. Z. Cai, J. Mol. Catal. A, 2009, 298, 94-98.
15. [15]
  [15] P. Braunstein, F. Naud, Angew. Chem. Int. Ed., 2001, 40, 680-699.
16. [16]
  [16] C. R. R Gan, Z. L. Liu, S. Q. Bai, K. S Ong, T. S. A. Hor, Dalton Trans., 2014, 43, 1821-1828.
17. [17]
  [17] S. Yokota, K. Tsujimoto, S. Hayashi, F. Pointillart, L. Ouahab, H. Fujiwara, Inorg. Chem., 2013, 52, 6543-6550.
18. [18]
  [18] C. W. Machan, A. M. Lifschitz, C. L. Stern, A. A. Sarjeant, C. A. Mirkin, Angew. Chem. Int. Ed., 2012, 51, 1469-1472.
19. [19]
  [19] R. Lindner, B. van den Bosch, M. Lutz, J. N. H. Reek, J. I. van der Vlugt, Organometallics, 2011, 30, 499-510.
20. [20]
  [20] R. Grigg, S. P. Mutton, Tetrahedron, 2010, 66, 5515-5548.
21. [21]
  [21] A. Brennführer, H. Neumann, M. Beller, Angew. Chem. Int. Ed., 2009, 48, 4114-4133.
22. [22]
  [22] J. R. Harjani, T. J. Abraham, A. T. Gomez, M. T. Garcia, R. D. Singer, P. J. Scammells, Green Chem., 2010, 12, 650-655.
23. [23]
  [23] T. E. Kunene, P. B. Webb, D. J. Cole-Hamilton, Green Chem., 2011, 13, 1476-1481.
24. [24]
  [24] C. Kolbeck, N. Paape, T. Cremer, P. S. Schulz, F. Maier, H. P. Steinrueck, P. Wasserscheid, Chem. Eur. J., 2010, 16, 12083-12087.
25. [25]
  [25] P. Wasserscheid, H. Waffenschmidt, P. Machnitzki, K. W. Kottsieper, O. Stelzer, Chem. Commun., 2001, 451-452.
26. [26]
  [26] R. P. J. Bronger, S. M. Silva, P. C. J. Kamer, P. W. N. M. van Leeuwen, Chem. Commun., 2002, 3044-3045.
27. [27]
  [27] J. Zhang, Y. Y. Wang, X. L. Zhao, Y. Liu, Eur. J. Inorg. Chem., 2014, 975-985.
28. [28]
  [28] Y. Canac, N. Debono, C. Lepetit, C. Duhayon, R. Chauvin, Inorg. Chem., 2011, 50, 10810-10819.
29. [29]
  [29] S. J. Lai, Y. Q. Li, H. Zhang, X. L. Zhao, Y. Liu, Catal. Commun., 2015, 58, 169-173.
30. [30]
  [30] D. W. Allen, B. F. Taylor, J. Chem. Soc., Dalton Trans., 1982, 51-54.
31. [31]
  [31] A. Suárez, M. A. Méndez-Rojas, A. Pizzano, Organometallics, 2002, 21, 4611-4621.
32. [32]
  [32] B. Milde, D. Schaarschmidt, T. Rüffer, H. Lang, Dalton Trans., 2012, 41, 5377-5390.
33. [33]
  [33] R. Oilunkaniemi, R. S. Laitinen, M. S. Hannu-Kuure, M. Ahlgrén, J. Organomet. Chem., 2003, 678, 95-101.
1. [1]
  Yameen Ahmed , Xiangxiang Feng , Yuanji Gao , Yang Ding , Caoyu Long , Mustafa Haider , Hengyue Li , Zhuan Li , Shicheng Huang , Makhsud I. Saidaminov , Junliang Yang . Interface Modification by Ionic Liquid for Efficient and Stable FAPbI₃ Perovskite Solar Cells. Acta Physico-Chimica Sinica, 2024, 40(6): 2303057-0. doi: 10.3866/PKU.WHXB202303057
2. [2]
  Hua Yu , Dingdu Chen , Xuan Wang , Lijun Yang , Geming Wang , Pu Hu . MOF-encapsulated phosphorus/nitrogen ionic liquid as a multifunctional flame-retardant additive for high-safety lithium-ion batteries. Acta Physico-Chimica Sinica, 2026, 42(7): 100201-. doi: 10.1016/j.actphy.2025.100201
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]
  Qiaorong RU . Synthesis and characterization of tripyridine functionalized polyionic liquid luminescent materials. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 111-119. doi: 10.11862/CJIC.20250121
5. [5]
  Wenjun Zheng . Application in Inorganic Synthesis of Ionic Liquids. University Chemistry, 2024, 39(8): 163-168. doi: 10.3866/PKU.DXHX202401020
6. [6]
  Linjie ZHU , Xufeng LIU . Electrocatalytic hydrogen evolution performance of tetra-iron complexes with bridging diphosphine ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 321-328. doi: 10.11862/CJIC.20240207
7. [7]
  Xuyu WANG , Xinran XIE , Dengke CAO . Photoreaction characteristics and luminescence modulation in phosphine-anthracene-based Au(Ⅰ) and Ir(Ⅲ) complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1513-1522. doi: 10.11862/CJIC.20250113
8. [8]
  Linjie ZHU , Xufeng LIU . Synthesis, characterization and electrocatalytic hydrogen evolution of two di-iron complexes containing a phosphine ligand with a pendant amine. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 939-947. doi: 10.11862/CJIC.20240416
9. [9]
  Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . Effect of Interlayer Anions in Layered Double Hydroxides on the Photothermocatalytic CO₂ Methanation of Derived Ni-Al₂O₃ Catalysts. Acta Physico-Chimica Sinica, 2025, 41(1): 100002-0. doi: 10.3866/PKU.WHXB202309002
10. [10]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
11. [11]
  Ranhui Fu , Shixin Zhou , Ran Ji , Feifei Gao , Hui Xu . 季膦盐合成实验的改进与拓展——水相一步法合成乙基三苯基溴化膦及其力致发光锰配合物的制备及表征. University Chemistry, 2026, 41(5): 252-263. doi: 10.12461/PKU.DXHX202510018
12. [12]
  Qilu DU , Li ZHAO , Peng NIE , Bo XU . Synthesis and characterization of osmium-germyl complexes stabilized by triphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1088-1094. doi: 10.11862/CJIC.20240006
13. [13]
  Hongjie SHEN , Haozhe MIAO , Yuhe YANG , Yinghua LI , Deguang HUANG , Xiaofeng ZHANG . Synthesis, crystal structure, and fluorescence properties of two Cu(Ⅰ) complexes based on pyridyl ligand. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 855-863. doi: 10.11862/CJIC.20250009
14. [14]
  Cunling Ye , Xitong Zhao , Hongfang Wang , Zhike Wang . A Formula for the Calculation of Complex Concentrations Arising from Side Reactions and Its Applications. University Chemistry, 2024, 39(4): 382-386. doi: 10.3866/PKU.DXHX202310043
15. [15]
  Yingran Liang , Fei Wang , Jiabao Sun , Hongtao Zheng , Zhenli Zhu . Construction and Application of a New Experimental Device for Determination of Alkaline Metal Elements by Plasma Atomic Emission Spectrometry Based on Solution Cathode Glow Discharge: An Alternative Approach for Fundamental Teaching Experiments in Emission Spectroscopy. University Chemistry, 2024, 39(5): 380-387. doi: 10.3866/PKU.DXHX202312024
16. [16]
  Rui Li , Huan Liu , Yinan Jiao , Shengjian Qin , Jie Meng , Jiayu Song , Rongrong Yan , Hang Su , Hengbin Chen , Zixuan Shang , Jinjin Zhao . Emerging Irreversible and Reversible Ion Migrations in Perovskites. Acta Physico-Chimica Sinica, 2024, 40(11): 2311011-0. doi: 10.3866/PKU.WHXB202311011
17. [17]
  Rongzhan LOU , Qiaoling KANG , Zhenchao BAI , Dongyun LI , Yang XU , Rui WANG , Qingyi LU . Research progress of sodium ion high entropy layered oxide cathode. Chinese Journal of Inorganic Chemistry, 2025, 41(12): 2411-2428. doi: 10.11862/CJIC.20250142
18. [18]
  Li Peicai , Wang Xubin , Zhang Qinghua , Wang Bowen , Rong Xiaohui , Hu Yong-Sheng , Li Zhongtao . High-rate and long-cycling P2-type cathode material for sodium-ion batteries. Acta Physico-Chimica Sinica, 2026, 42(5): 100214-. doi: 10.1016/j.actphy.2025.100214
19. [19]
  Feiya Cao , Qixin Wang , Pu Li , Zhirong Xing , Ziyu Song , Heng Zhang , Zhibin Zhou , Wenfang Feng . Magnesium-Ion Conducting Electrolyte Based on Grignard Reaction: Synthesis and Properties. University Chemistry, 2024, 39(3): 359-368. doi: 10.3866/PKU.DXHX202308094
20. [20]
  Ke Zhao , Zhen Liu , Luyao Liu , Changyuan Yu , Jingshun Pan , Xuguang Huang . Functionalized Reflective Structure Fiber-Optic Interferometric Sensor for Trace Detection of Lead Ions. Acta Physico-Chimica Sinica, 2024, 40(4): 2304029-0. doi: 10.3866/PKU.WHXB202304029

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1015)
HTML views(69)

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