Chinese Journal of Organic Chemistry >
Study on the Synthesis of Oxyresveratrol Catalyzed by Palladium
Received date: 2015-09-30
Revised date: 2015-12-03
Online published: 2016-01-04
Supported by
Project supported by the Natural Science Foundation of Hunan Province (No. 2015JJ3012), the Scientific Research Fund of Hunan Provincial Education Department (No. 14C0050) and Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation (2016CL01).
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.
Key words： decarboxylation; oxyresveratrol; palladium catalysis; heck reaction
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
[1] Li, H. T.; Cheng, K. W.; Cho, C. H.; He, Z. D.; Wang, M. F. J. Agric. Food Chem. 2007, 55, 2604.
[2] Park, J.; Park, J. H.; Suh, H. J.; Lee, I. C.; Koh, J.; Boo, Y. C. Arch. Dermatol. Res. 2014, 306, 475.
[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] Suhee, S.; Hyojin, L.; Youngeup, J.; Young, M. H.; Sungjin, B.; Hae, Y. C.; Hongsuk, S. Bioorg. Med. Chem. Lett. 2007, 17, 461.
[5] Taksina, C.; Jurairatana, P.; Vimolmas, L.; Kittisak, L.; Mikiko, S.; Pornpen, P.; Masao, H.; Kimiyasu, S. Antiviral Res. 2008, 80, 62.
[6] Choi, S. Y.; Kim, S.; Hwang, J. S.; Lee, B. G.; Kim, H.; Kim, S. Y. Biochem.Pharmacol. 2004, 67, 707.
[7] Sun, H. Y.; Xiao, C. F.; Wen, W.; Chen, Y.; Lü, Z. L.; Zou, Y. Chin. J. Org. Chem. 2010, 30, 1574 (in Chinese).
(孙洪宜, 肖春芬, 魏文, 陈煜, 吕泽良, 邹永, 有机化学, 2010, 30, 1574.)
[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] Wu, X. F.; Anbarasan, P.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2010, 49, 9047.
[10] Oestreich, M. The Mizoroki-Heck Reaction, Wiley, Weinheim, 2009, Chapter 1.
[11] Fu, Z. J.; Li, Z. J.; Xiong, Q. H.; Cai, H. Chin. J. Org. Chem. 2015, 35, 984 (in Chinese).
(付拯江, 李兆杰, 熊起恒, 蔡琥, 有机化学, 2015, 35, 984.)
[12] Zhou, Q. Z.; Zhang, B.; Chen, D.; Chen, R. E.; Jiang, H. J. Chin. J. Org.Chem.2011, 31, 2181 (in Chinese).
(周其忠, 张斌, 陈丹, 陈仁尔, 蒋华江, 有机化学, 2011, 31, 2181.)
[13] Prakash, G. K. S.; Jog, P. V.; Krishnan, H. S.; Olah, G. A. J. Am. Chem. Soc. 2011, 133, 2140.
[14] Shard, A.; Sharma, N.; Bharti, R.; Dadhwal, S.; Kumar, R.; Sinha, A. K. Angew. Chem., Int. Ed. 2012, 51, 12250.
[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] Albadi, J.; Abedini, M.; Iravani, N. Chin. Chem. Lett.2012, 23, 261.
[17] Tuba, A.; Ahmet, C.; Cavit, K.; Neslihan, B.; Yasin, B.; Yavuz, T. Chem. Biodiversity 2014, 8, 1192.
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