Citation: Jiong Wang, Bing Mu, Zhihua Fu, Li Wang, Tiesheng Li, Yangjie Wu. Cyclopalladated ferrocenylimines with ester groups for Heck and Suzuki coupling reactions[J]. Chinese Journal of Catalysis, ;2014, 35(7): 1059-1067. doi: 10.1016/S1872-2067(14)60045-0 shu

Cyclopalladated ferrocenylimines with ester groups for Heck and Suzuki coupling reactions

Jiong Wang ^a ,
Bing Mu ^b ,
Zhihua Fu ^a ,
Li Wang ^a ,
Tiesheng Li ^a,, ,
Yangjie Wu ^a,,

1.
a. The College of Chemistry and Molecular Engineering, The Key Lab of Chemical Biology and Organic Chemistry of Henan Province, The Key Lab of Advanced Nano-information Materials of Zhengzhou, Zhengzhou University, Zhengzhou 450001, Henan, China;

Corresponding author: Tiesheng Li, Yangjie Wu,
Received Date: 10 October 2013
Available Online: 22 January 2014
Fund Project:

Cyclopalladated ferrocenylimine dimers and cyclopalladated ferrocenylimine monomers were designed and prepared. They were characterized using ¹H NMR, ¹³C NMR, and IR spectroscopies, and MS. The catalytic properties of these compounds in Heck and Suzuki coupling reactions in water or organic solvents were systematically investigated. The results showed that these catalysts could effectively catalyze Heck and Suzuki coupling reactions of aryl or heteroaryl halides in water or organic solvents.
- Heck coupling reaction,
- Suzuki coupling reaction,
- Cyclopalladated ferrocenylimine
1. [1]
  [1] Suzuki A. J Organomet Chem, 1999, 576: 147
2. [2]
  [2] Wolfe J P, Singer R A, Yang B H, Buchwald S L. J Am Chem Soc, 1999, 121: 9550
3. [3]
  [3] Miyaura N. Top Curr Chem, 2002, 219: 11
4. [4]
  [4] Hassan J, Sevignon M, Gozzi C, Schulz E, Lemaire M. Chem Rev, 2002, 102: 1359
5. [5]
  [5] Stille J K. Angew Chem Int Ed, 1986, 25: 508
6. [6]
  [6] Beller M, Fischer H, Herrmannl W A, öfele K, Brossmer1 C, Reisinger C P, Priermeier T. Angew Chem Int Ed, 1995, 34: 1848
7. [7]
  [7] Sheldon R A, van Bekkum H. Fine Chemicals through Hetero-geneous Catalysis. Weinheim: Wiley-VCH, 2001
8. [8]
  [8] Nicolaou K C, Boddy C N C, Brase S, Winssinger N. Angew Chem Int Ed, 1999, 38: 2096
9. [9]
  [9] Baudoin O, Cesario M, Guenard D, Gueritte F. J Org Chem, 2002, 67: 1199
10. [10]
  [10] Beletskaya I P, Cheprakov A V C. Chem Rev, 2000, 100: 3009
11. [11]
  [11] Yao Q W, Kinney E P, Yang Z. J Org Chem, 2003, 68: 7528
12. [12]
  [12] Zhao N, Wang F, Zhou M L, Li T S, Liu H, Xu W J, Wu Y J. Chin J Catal (赵娜, 王飞, 周梅玲, 李铁生, 刘辉, 许文俭, 吴养洁. 催化学报), 2013, 34: 1583
13. [13]
  [13] Ge Y C, Cheng Y J, Fu H Y, Zheng X L, Li R X, Chen H, Li X J. Chin J Catal (葛轶苓, 程雨晶, 付海燕, 郑学丽, 李瑞祥, 陈华, 李贤均. 催化学报), 2013, 34: 1667
14. [14]
  [14] Kovala-Demertzi D, Yadav P N, Demertzis M A, Jasiski J P, Andreadaki F J, Kostas I D. Tetrahedron Lett, 2004, 45: 2923
15. [15]
  [15] Tundo P, Anastas P, Black D S, Breen J, Collins T, Memoli S, Miyamoto J, Polyakoff M, Tumas W. Pure Appl Chem, 2000, 72: 1207
16. [16]
  [16] Liu L F, Zhang Y H, Wang Y G. J Org Chem, 2005, 70: 6122
17. [17]
  [17] Liu L F, Zhang Y H, Xin B W. J Org Chem, 2006, 71: 3994
18. [18]
  [18] Li H, Wu Y J. Appl Organomet Chem, 2008, 22: 233
19. [19]
  [19] Zhou J, Guo X M, Tu C Z, Li X Y, Sun H J. J Organomet Chem, 2009, 694: 697
20. [20]
  [20] Saha D, Chattopadhyay K, Ranu B C. Tetrahedron Lett, 2009, 50: 1003
21. [21]
  [21] Basu B, Biswas K, Kundu S, Ghosh S. Green Chem, 2010, 12: 1734
22. [22]
  [22] Veerakumar P, Velayudham M, Lu K L, Rajagopal S. Appl Catal A, 2013, 455: 247
23. [23]
  [23] Wójcik K, Goux-Henry C, Andrioletti B, Pietrusiewicz K M, Framery E. Tetrahedron Lett, 2012, 53: 5602
24. [24]
  [24] Konovets A, Penciu A, Framery E, Percina N, Goux-Henry C, Sinou D. Tetrahedron Lett, 2005, 46: 3205
25. [25]
  [25] Shang Y J, Wu J W, Fan C L, Hu J S, Lu B Y. J Organomet Chem, 2008, 693: 2963
26. [26]
  [26] Mu B, Li J Y, Han Z X, Wu Y J. J Organomet Chem, 2012, 700: 117
27. [27]
  [27] Schönfelder D, Nuyken O, Weberskirch R. J Organomet Chem, 2005, 690: 4648
28. [28]
  [28] Susanto W, Chu C Y, Ang W J, Chou T C, Lo L C, Lam Y. J Org Chem, 2012, 77: 2729
29. [29]
  [29] Zhang J L, Yang F, Ren G R, Mak T C W, Song M P, Wu Y J. Ultrason Sonochem, 2008, 15: 115
30. [30]
  [30] Marziale A N, Jantke D, Faul S H, Reiner T, Herdtweck E, Eppinger J. Green Chem, 2011, 13: 169
31. [31]
  [31] Yang J H, Wang D F, Liu W D, Zhang X, Bian F L, Yu W. Green Chem, 2013, 15: 3429
32. [32]
  [32] El Bakouri O, Fernández M, Brun S, Pla-Quintana A, Roglans A. Tetrahedron, 2013, 69: 9761
33. [33]
  [33] Mu B, Li T S, Li J Y, Wu Y J. J Organomet Chem, 2008, 693: 1243
34. [34]
  [34] Mu B, Li T S, Fu Z H, Wu Y J. Catal Commun, 2009, 10: 1497
35. [35]
  [35] Yu A J, Shen L, Cui X L, Peng D P, Wu Y J. Tetrahedron, 2012, 68: 2283
36. [36]
  [36] Huang M M, Feng Y J, Wu Y J. Tetrahedron, 2012, 68: 376
37. [37]
  [37] Zhang J L, Yang X Q, Cui X L, Wu Y J. Tetrahedron, 2011, 67: 8800
38. [38]
  [38] Leng Y T, Yang F, Zhu W G, Zou D P, Wu Y J, Cai R R. Tetrahedron, 2011, 67: 6191
39. [39]
  [39] Mu B, Li T S, Li C H, Liu P P, Shang W, Wu Y J. Tetrahedron, 2009, 65: 2599
40. [40]
  [40] Yang F, Cui X L, Li Y N, Zhang J L, Ren G R, Wu Y J. Tetrahedron, 2007, 63: 1963
41. [41]
  [41] Li J Y, Cui M J, Yu A J, Wu Y J. J Organomet Chem, 2007, 692: 3732
1. [1]
  Senqiang Zhu , Ruohan Li , Yujia Yang , Jinzhi Liao , Rui Liu . 聚光成辉——Suzuki偶联反应高效制备聚集诱导发射荧光分子及其潜指纹识别应用. University Chemistry, 2026, 41(5): 109-119. doi: 10.12461/PKU.DXHX202511066
2. [2]
  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
3. [3]
  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
4. [4]
  Kexin Feng , Jie Zhang , Yujia Sun , Qiong Ai , Longchun Li . 乙酰二茂铁和二茂铁甲酰丙酮的合成、纯化及表征. University Chemistry, 2025, 40(8): 307-314. doi: 10.12461/PKU.DXHX202409045
5. [5]
  Zhang Xiaofei , Xu Shanhao , Wang Zhiyuan , He Long , Huang Tangcheng , Xu Yongming , Bian Yucui , Li Yike , Chen Haijun , Li Zhongjun . Surface doping of graphene into BiOCl for efficient photocatalytic amine coupling under visible light. Acta Physico-Chimica Sinica, 2026, 42(5): 100202-. doi: 10.1016/j.actphy.2025.100202
6. [6]
  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
7. [7]
  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): 100038-0. doi: 10.3866/PKU.WHXB202408015
8. [8]
  Jianfeng Yan , Yating Xiao , Xin Zuo , Caixia Lin , Yaofeng Yuan . Comprehensive Chemistry Experimental Design of Ferrocenylphenyl Derivatives. University Chemistry, 2024, 39(4): 329-337. doi: 10.3866/PKU.DXHX202310005
9. [9]
  Guilan He , Yaofeng Yuan . 手性二茂铁双膦配体Xyliphos的合成及应用. University Chemistry, 2025, 40(8): 130-137. doi: 10.12461/PKU.DXHX202409122
10. [10]
  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
11. [11]
  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
12. [12]
  Haoqi Zhang , Borui Yao , Yun Zhang , Zhiguang Song , Bo Wang . 通过格氏试剂与环氧苯乙烯的反应认识其组成与性质的复杂性. University Chemistry, 2026, 41(5): 50-61. doi: 10.12461/PKU.DXHX202511129
13. [13]
  Ying Wang , Mingcheng Yang , Zhu Yin , Yingqi Wang , Jiajia Cheng . Transition metal-free poly(heptazine imide) photocatalyst for C-X bond construction from katritzky salts. Acta Physico-Chimica Sinica, 2026, 42(7): 100212-. doi: 10.1016/j.actphy.2025.100212
14. [14]
  Chengqian Mao , Yanghan Chen , Haotong Bai , Junru Huang , Junpeng Zhuang . Photodimerization of Styrylpyridinium Salt and Its Application in Silk Screen Printing. University Chemistry, 2024, 39(5): 354-362. doi: 10.3866/PKU.DXHX202312014
15. [15]
  Jiageng Li , Putrama . 数值积分耦合非线性最小二乘法一步确定反应动力学参数. University Chemistry, 2025, 40(6): 364-370. doi: 10.12461/PKU.DXHX202407098
16. [16]
  Mengfan Gong , Dongju Zhang . Estimating Delocalization Energies of 1,3-Butadiene and Benzene with Isodesmic Reactions: A Relatively Precise Approach. University Chemistry, 2026, 41(4): 457-463. doi: 10.12461/PKU.DXHX202505036
17. [17]
  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
18. [18]
  Chao WU , Qingxiu SHI , Tao XU , Zhengxi PENG , Zhongping XIONG , Yinglin ZHANG , Yujun SI , Chaozhong GUO . Enhancement of oxygen reduction reaction performance of iron-nitrogen doped carbon based catalysts by sodium carboxymethyl cellulose pre-deoxygenation. Chinese Journal of Inorganic Chemistry, 2026, 42(4): 737-746. doi: 10.11862/CJIC.20250305
19. [19]
  Yawei Li , Siming Li , Fuhao Duan , Xuran Wang , Yangyang Zhao , Yue Zhang , Wei Guo , Junsheng Hao . 基于旋转电极双通道新方法的铁氰化钾电化学反应过程分析改进实验. University Chemistry, 2026, 41(5): 91-100. doi: 10.12461/PKU.DXHX202511082
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1001)
HTML views(64)

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