Study on the Synthesis of Oxyresveratrol Catalyzed by Palladium

doi:10.6023/cjoc201509046

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (5): 1143-1147.DOI: 10.6023/cjoc201509046 Previous Articles Next Articles

NOTE

钯催化合成氧化芪三酚的研究

李志伟^a, 康绍英^b, 陈琳^a, 王宇^a, 李江胜^a

a. 电力与交通材料保护湖南省重点实验室长沙理工大学化学与生物工程学院长沙 410114;
b. 湖南省食品质量监督检验研究院长沙 410111

收稿日期:2015-09-30 修回日期:2015-12-03 发布日期:2016-01-04
通讯作者: 李志伟, 李江胜 E-mail:lizwhn@126.com;jslichem@gmail.com
基金资助:
湖南省自然科学基金(No.2015JJ3012)、湖南省教育厅(No.14C0050)和电力与交通材料保护湖南省重点实验室(No.2016CL01)资助项目.

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

Received:2015-09-30 Revised:2015-12-03 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

Cite this article

Li Zhiwei, Kang Shaoying, Chen Lin, Wang Yua, Li Jiangsheng. Study on the Synthesis of Oxyresveratrol Catalyzed by Palladium[J]. Chin. J. Org. Chem., 2016, 36(5): 1143-1147.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[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.

钯催化合成氧化芪三酚的研究

Study on the Synthesis of Oxyresveratrol Catalyzed by Palladium

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Hongqiong Zhao, Miao Yu, Dongxue Song, Qi Jia, Yingjie Liu, Yubin Ji, Ying Xu. Progress on Decarboxylation and Hydroxylation of Carboxylic Acids [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 70-84.
[2]	Jingrui Wang, Yongkui Feng, Nengzhong Wang, Nianyu Huang, Hui Yao. Pd-Catalyzed Stereoselective Synthesis of Nitroalkyl β-C-Glycosides [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3216-3225.
[3]	Wei Xu, Hongbin Zhai, Bin Cheng, Taimin Wang. Visible Light-Induced Pd-Catalyzed Heck Reactions [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3035-3054.
[4]	Yuchao Wang, Jinbiao Liu, Zhitao He. Palladium-Catalyzed Asymmetric Hydrofunctionalizations of Conjugated Dienes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2614-2627.
[5]	Yi Wang, Jian Zhang, Yangzi Liu, Xiaoyan Luo, Weiping Deng. Palladium-Catalyzed Asymmetric [3＋4] Cycloadditions for the Construction of Cyclohepta[b]indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2864-2877.
[6]	Yongling Wang, Tiexin Zhang, Xuming Zhang, Hanyang Sun, Jinyao Leng, Yaming Li. Synthesis of Unnatural Amino Acid Derivatives by Visible- Light-Catalyzed Decarboxylative Alkylation of N-Aromatic Glyoxylimines [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4284-4293.
[7]	Wei Xiong, Bin Shi, Xuan Jiang, Liangqiu Lu, Wenjing Xiao. Ligand-Switched Pd-Catalyzed Divergent Transformations of Vinyl Cyclic Carbamates and Isocyanates [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 265-273.
[8]	Xuqun Zeng, Qian Zhang, Xufeng Wu, Jingfeng Zhang, Xinwei Zhang, Xiaolei Huang. Nickel-Catalyzed Heck Reaction of Cycloalkenes with Inert C—O Bonds of Aryl Carbonates and Aryl Sulfamates [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2981-2987.
[9]	Hong-Chao Chen, Yichen Wu, Yang Yu, Peng Wang. Pd-Catalyzed Isomerization of Alkenes [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 742-757.
[10]	Xintuo Yang, Pinhong Chen, Guosheng Liu. Asymmetric Palladium-Catalyzed Aza-Wacker Reaction of Alkenes: Efficient Synthesis of Chiral 1,3-Oxazinan-2-ones [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3382-3389.
[11]	Shihu Jia, Siyuan Chen, Zeshui Liu, Honggang Cheng, Qianghui Zhou. Pd/Novel Axially Chiral Phosphine-Alkene Ligands Catalyzed Asymmetric Allylic Alkylation of Indoles [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3373-3381.
[12]	Jieming Zhang, Hang Ni, Qi Wu, Junfeng Yang, Junliang Zhang. Development of P, S and Si-Stereogenic Compounds Synthesis via Palladium Catalysis [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3118-3128.
[13]	Zhengjiang Fu, Xihan Cao, Jian Yin, Zhenyu Gou, Xuezheng Yi, Hu Cai. ortho-C—H Bond Functionalization of Carboxylic Acid Using Carboxyl as a Traceless Directing Group Based on the Strategy of “Two Birds with One Stone” [J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 67-74.
[14]	Xiao Xiao, Jianchao Liu. Progress in the Synthesis of C(sp²)—C(sp³) Bond by Reductive Heck Reactions of Alkenes [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3349-3365.
[15]	Tao Zhang, Shangda Li, Chunlin Zhou, Xinchao Wang, Meng Zhang, Zezhong Gao, Gang Li. Site-Selective C—H Iodination of Phenol Derivatives Using Aryl Iodide as Iodinating Reagent [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3511-3520.