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
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