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Citation: Li Zhiwei, Kang Shaoying, Chen Lin, Wang Yua, Li Jiangsheng. Study on the Synthesis of Oxyresveratrol Catalyzed by Palladium[J]. Chinese Journal of Organic Chemistry, ;2016, 36(5): 1143-1147. doi: 10.6023/cjoc201509046 shu

Study on the Synthesis of Oxyresveratrol Catalyzed by Palladium

Li Zhiwei ^a,*,, ,
Kang Shaoying ^b ,
Chen Lin ^a ,
Wang Yua ^a ,
Li Jiangsheng ^a,*,,

a.
Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation, School of Chemistry and Biological Engineering, Changsha University of Science and Technology, Changsha 410114
b.
Hunan Institute of Food Quality Supervision Inspection and Research, Changsha 410111

Corresponding author: Li Zhiwei, lizwhn@126.com Li Jiangsheng, jslichem@gmail.com
Received Date: 30 September 2015
Revised Date: 3 December 2015

Fund Project: Project supported by the Natural Science Foundation of Hunan Province No. 2015JJ3012and Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation 2016CL01the Scientific Research Fund of Hunan Provincial Education Department No. 14C0050

Figures(2)

A convenient method for the synthesis of oxyresveratrol catalyzed by palladium is described. 2,4-Dihydroxyiodo-benzene underwent Heck reaction with acrylic acid, then decarboxylation, and further underwent Heck reaction with 3,5-dihydroxyiodobenzene, furnishing oxyresveratrol in a high yield. The title compound was characterized by MS and NMR. This synthetic method has several advantages such as less step processes, high yield, simple operations, and promises to be applied in industrial production.
- oxyresveratrol,
- palladium catalysis,
- heck reaction,
- decarboxylation
1. [1]
  Li, H. T.; Cheng, K. W.; Cho, C. H.; He, Z. D.; Wang, M. F. J. Agric. Food Chem. 2007, 55, 2604.
2. [2]
  Park, J.; Park, J. H.; Suh, H. J.; Lee, I. C.; Koh, J.; Boo, Y. C. Arch. Dermatol. Res. 2014, 306, 475.
3. [3]
  Weber, J. T.; Lamont, M.; Chibrikova, L.; Fekkes, D.; Vlug, A. S.; Lorenz, P.; Kreutzmann, P.; Slemmer, J. E. Eur. J. Pharmacol,2012, 680, 55.
4. [4]
  Suhee, S.; Hyojin, L.; Youngeup, J.; Young, M. H.; Sungjin, B.; Hae, Y. C.; Hongsuk, S. Bioorg. Med. Chem. Lett. 2007, 17, 461.
5. [5]
  Taksina, C.; Jurairatana, P.; Vimolmas, L.; Kittisak, L.; Mikiko, S.; Pornpen, P.; Masao, H.; Kimiyasu, S. Antiviral Res. 2008, 80, 62.
6. [6]
  Choi, S. Y.; Kim, S.; Hwang, J. S.; Lee, B. G.; Kim, H.; Kim, S. Y. Biochem.Pharmacol. 2004, 67, 707.
7. [7]
8. [8]
  Zheng, Q. Y.; Li, Z. W.; Xie, Z. Y.; Bao, Z. C.; Wang, J. N. CN 103172499,2013[Chem. Abstr. 2013, 159, 181645].
9. [9]
  Wu, X. F.; Anbarasan, P.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2010, 49, 9047.
10. [10]
  Oestreich, M. The Mizoroki-Heck Reaction, Wiley, Weinheim, 2009, Chapter 1.
11. [11]
12. [12]
13. [13]
  Prakash, G. K. S.; Jog, P. V.; Krishnan, H. S.; Olah, G. A. J. Am. Chem. Soc. 2011, 133, 2140.
14. [14]
  Shard, A.; Sharma, N.; Bharti, R.; Dadhwal, S.; Kumar, R.; Sinha, A. K. Angew. Chem., Int. Ed. 2012, 51, 12250.
15. [15]
  Mao, W. W.; Wang, T. T.; Zeng, H. P.; Wang, Z. Y.; Chen, J. P.; Shen, J. G. Bioorg.Med. Chem. Lett.2009, 19, 4570.
16. [16]
  Albadi, J.; Abedini, M.; Iravani, N. Chin. Chem. Lett.2012, 23, 261.
17. [17]
  Tuba, A.; Ahmet, C.; Cavit, K.; Neslihan, B.; Yasin, B.; Yavuz, T. Chem. Biodiversity 2014, 8, 1192.
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