Synthesis of Phenols under Mild Conditions in Water Using Recyclable Chitosan@Copper as Catalyst

doi:10.6023/cjoc201510027

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (4): 862-866.DOI: 10.6023/cjoc201510027 Previous Articles Next Articles

NOTE

水相中由壳聚糖-铜催化合成苯酚的方法研究

赵苏艳^a, 王祖利^b

a. 吉林警察学院实验技术中心长春 130117;
b. 青岛农业大学化学与药学院青岛 266109

收稿日期:2015-10-23 修回日期:2015-11-16 发布日期:2015-12-10
通讯作者: 王祖利 E-mail:wangzulichem@163.com
基金资助:
国家自然科学基金(No.21402103)、山东省优秀中青年基金(No.BS2013YY024)、中国博士后基金(No.150030)资助项目.

Synthesis of Phenols under Mild Conditions in Water Using Recyclable Chitosan@Copper as Catalyst

Zhao Suyan^a, Wang Zuli^b

a. Jilin Police College Experimental Technology Center, Changchun 130117;
b. College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109

Received:2015-10-23 Revised:2015-11-16 Published:2015-12-10
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21402103), the Scientific Research Foundation of Shandong Province Outstanding Young Scientist Award (No. BS2013YY024), and the Postdoctoral Science Foundationof China (No. 150030).

1. Synthesis of Phenols under Mild Conditions in Water Using Recyclable Chitosan@Copper as Catalyst.PDF(1943KB)

Cite this article

Zhao Suyan, Wang Zuli. Synthesis of Phenols under Mild Conditions in Water Using Recyclable Chitosan@Copper as Catalyst[J]. Chin. J. Org. Chem., 2016, 36(4): 862-866.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

[1] Rappoport, Z. The Chemistry of Phenols, Wiley-VCH, Weinheim,Germany, 2003.
[2] Zhang, R. X.; Zhang, X. D. Chemical Industry 2008, 26, 47 (in Chinese). (张日新, 张晓东, 化学工业, 2008, 26, 47.)
[3] (a) Anderson, K. W.; Ikawa, T. R.; Tundel, E. S.; Buchwald, L. J. Am. Chem. Soc.2006, 128, 10694.
(b) Willis, M. C. Angew. Chem., Int. Ed. 2007, 46, 3402.
(c) Sergeev, A. G.; Schulz, T.; Torborg, C.; Spannenberg, A.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 7595.
(d) Schulz, T.; Torborg, C.; Schäffner, B.; Huang, J.; Zapf, A.; Kadyrov, R.; Börner, A.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 918.
(e) Gallon, B. J.; Kojima, R. W.; Kaner, R. B.; Diaconescu, P. L. Angew. Chem., Int. Ed. 2007, 46, 7251.
(f) Chen, G. S.; Chan, A. S. C.; Kwong, F. Y. Tetrahedron Lett. 2007, 48, 473.
[4] (a) Yang, D. S.; Fu, H. Chem. Eur. J. 2010, 16, 2366.
(b) Kormos, C. M.; Leadbeater, N. E. Tetrahedron 2006, 62, 4728;
(c) Tlili, A.; Xia, N.; Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 8725.
(d) Zhao, D. B.; Wu, N. J.; Zhang, S.; Xi, P.; Su, X. Y.; Lan, J. B.; You, J. S. Angew. Chem., Int. Ed. 2009, 48, 8729.
[5] Yin, L.; Leibescher, J. Chem. Rev. 2007, 107, 133.
[6] Li, B.; Li, M.; Yao, C. H.; Shi, Y. F.; Ye, D. R.; Wu, J.; Zhao, D. Y. J. Mater. Chem. 2013, 1, 6742.
[7] For selected examples, see: (a) Kantam, M. L.; Yadav, Y.; Laha, Y.; Srinivas, P.; Sreedhar, B.; Figueras, F. J. Org. Chem. 2009, 74, 4608.
(b) Kundu, D.; Chatterjee, T.; Ranu, B. C. Adv. Synth. Catal. 2013, 355, 2285.
(c) Brahmachari, G.; Laskar, S.; Barik, P. RSC Adv. 2013, 3, 142;
(d) Parella, R.; Kumar, A; Babu, S. A. Tetrahedron Lett. 2013, 54, 1738.
(e) Yang, S.; Wu, C.; Zhou, H.; Yang, Y.; Zhao, Y.; Wang, C.; Yang, W.; Xu, J. Adv. Synth. Catal. 2013, 355, 53.
(f) Swapna, K.; Murthy, S. N.; Jyothi, M. T.; Nageswar, Y. V. D. Org. Biomol. Chem. 2011, 5989.
(g) Hudson, R.; Ishikawa, S.; Li, C.-J.; Moores, A. Synlett 2013, 1637.
(h) Dandia, A.; Jain, A. K.; Sharma, S. RSC Adv. 2013, 3, 2924.
(i) Kumar, A. S.; Reddy, M.; M.Knorn, A.; Reiser, O.; Sreedhar, B. Eur. J. Org. Chem. 2013, 4, 674.
(j) Wang, Z. L. RSC Adv. 2015, 5, 5563.
[8] Zhang, J.; Han, D.; Zhang, H.; Chaker, M.; Zhao, Y.; Ma, D. Chem. Commun. 2012, 48, 11510.
[9] (a) Makhubela, B. C. E.; Jardine, A.; Smith, G. S. Appl. Catal. 2011, 393, 231.
(b) Lasri, J.; Leod, T. C. O. M.; Pombeiro, A. J. L. Appl. Catal. 2011, 393, 94.
(c) Yi, S. S.; Lee, D. H.; Sin, E.; Lee, Y. S. Tetrahedron Lett. 2007, 48, 6771.
[10] (a) Shen, C.; Xu, J.; Yu, W.; Zhang, P. Green Chem. 2014, 16, 3007.
(b) Shen, C.; Xu, J.; Yu, W. B.; Zhang, P. F. Green Chem. 2014, 16, 3007.
[11] Yang, B.; Mao, Z. X.; Zhu, X. H.; Wan, Y. Q. Catal. Commun. 2015, 60, 92.
[12] Pal, M.; Parasuraman, K.; Yeleswarapu, K. R. Org. Lett. 2003, 5, 349.
[13] Molander, G. A.; Cavalcanti, L. N. J. Org. Chem. 2011, 76, 623.
[14] Jiang, M.; Yang, H. J.; Li, Y.; Jia, Z. Y.; Fu, H. Chin. Chem. Lett. 2014, 25, 715.
[15] Yang, D. S.; An, B. J.; Wei, W.; Jiang, M.; You, J. M.; Wang, H. Tetrahedron 2014, 70, 3630.
[16] Xu, J. M.; Wang, X. Y.; Shao, C. W.; Su, D. Y.; Cheng, G. L.; Hu, Y. F. Org. Lett. 2010, 12, 164.
[17] Tlili, A.; Xia, N.; Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 8725.

水相中由壳聚糖-铜催化合成苯酚的方法研究

Synthesis of Phenols under Mild Conditions in Water Using Recyclable Chitosan@Copper as Catalyst

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Xiantao Ma, Xiaoyu Yan, Yingying Zhu, Shuanglin Niu, Yuxuan Wang, Chao Yuan. Water-Promoted Green Synthesis of Heteroaryl Thioether [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2136-2142.
[2]	Wenting Wei, Zhuangzhuang Li, Wandi Li, Jiaqi Li, Xianying Shi. Green Method for Constructing Phthalides via Oxidative Coupling of Aromatic Acids and Acrylates in Neat Water and Air [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1177-1186.
[3]	Biao Han, Yaoyao Zhang, Shuhan Chen, Mengge Zhao, Nan Li, Weishuang Li, Lei Zhu. Preparation of Axially Grafted Temperature-Responsive Chiral Salen Mn^III and Application in Asymmetric Epoxidation of Olefins in Water [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 244-253.
[4]	Liping Pang, Changjie Yang, Hongmin Lin, Xinyu Li, Haitao Tang, Yingming Pan. Porous Organophosphine Ligand Polymers as Recyclable Ligands for the Synthesis of Isoindolinone Compounds [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2117-2123.
[5]	JIan Xiao, Zhiying Wu, Ziyi Chen, Pengfei Zhao. Tetraethylenepentamine Functionalized Phenolic Resin as Highly Active Acid-Base Bifunctional Catalyst for Knoevenagel Condensation Reaction [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1179-1187.
[6]	Donglan Liu, Haiyan Xu, Yi Hang, Hongfei Lu. 1,6-Addition of Nitrogen Nucleophile to para-Quinone Methides Catalyzed by Recyclable Bismuth Complex: Facile Access to N-Heterocyclic Substituted Unsymmetric Triarylmethane Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 796-802.
[7]	Xiaolong Zhao, Yuqing Li, Liangwu Guo, Qiyuan Ran, Huihui Wu, Zhen Zhang, Yingpeng Su, Pengxin Zhou, Na Yan. A Highly Selective and High-Contrast Colorimetric “Off-On” Chemosensor for Cu^2＋ Based on Boron-Dipyrromethene (BODIPY) Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3757-3765.
[8]	Ziqi Su, Qi Zhang, Jieqiang Zhao, Tao Zhao, Wenyi Liu, Huiping Wang, Juan Xu, Jiarong Li. An Efficient and Rapid Synthesis of 1H-Pyrazolo[3,4-d]-pyrimidin-4(5H)-one in Water [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3701-3709.
[9]	Huan Liu, Xufeng Lin, Da Yang. Novel Ir-Complexes for Hydroformylation of Olefins with H₂O as the Hydrogen Source [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3571-3577.
[10]	Xixi Zheng, Yunyun Liu, Jie-Ping Wan. Metal-Free Synthesis of 1,2,3-Triazoles in Pure Water via the Enamine Modified Annulation Reactions with Tosyl Azide [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2700-2706.
[11]	Mei Wu, Ling Yu, Huiqing Hou, Houzheng Chen, Qinglong Zhuang, Sunying Zhou, Xiaoyan Lin. Electrochemistry-Enabled Copper-Catalyzed Oxidation of Benzyl Alcohols for the Preparation of Quinazolinones in Water [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2326-2334.
[12]	Xiang Fang, Wang Wang, Xueyan Yang, Fanhong Wu. A Green Method for the Synthesis of Sulfones from Thioethers [J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 412-417.
[13]	Liu Renzhi, Yang Min, Qiu Guanyinsheng, Zhang Lianpeng, Wang Yuchao, Luo Jin. Base-Free 5-exo-dig aza-Cyclization of N-Methoxyl-2-alkynylbenzamides in Water [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 2071-2077.
[14]	Yang Yunhan, Bao Qiulian, Luo Jianping, Yang Junli, Li Canhua, Wei Keke, Chuan Yongming, Yang Lijuan. Competitive Fluorescence Sensing for Paraquat Based on Methylene Blue/Water-Soluble Phosphate Salt Pillar[5]arene [J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1680-1688.
[15]	Luo Liang, Cao Xiaomei, Lai Guowei, Liu Jinxiang, Luo Haiqing, Lu Dongliang, Zhang Yong. “On Water” Nucleophilic Addition of Pyrazolones to Trifluoromethyl Ketones [J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1323-1330.