Citation:
Zhao Suyan, Wang Zuli. Synthesis of Phenols under Mild Conditions in Water Using Recyclable Chitosan@Copper as Catalyst[J]. Chinese Journal of Organic Chemistry,
;2016, 36(4): 862-866.
doi:
10.6023/cjoc201510027
-
A green and efficient protocol for the synthesis of phenols using recyclable chitosan@copper as catalyst was developed. Phenols can be obtained in moderate to excellent yields. The catalyst can be recycled and reused for five times without significant loss of its catalytic activity.
-
Keywords:
- chitosan@copper,
- recyclable,
- phenylboronic acid,
- water
-
-
-
[1]
[1] Rappoport, Z. The Chemistry of Phenols, Wiley-VCH, Weinheim,Germany, 2003.
-
[2]
[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]
[3] (a) Anderson, K. W.; Ikawa, T. R.; Tundel, E. S.; Buchwald, L. J. Am. Chem. Soc.2006, 128, 10694.
-
[4]
(b) Willis, M. C. Angew. Chem., Int. Ed. 2007, 46, 3402.
-
[5]
(c) Sergeev, A. G.; Schulz, T.; Torborg, C.; Spannenberg, A.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 7595.
-
[6]
(d) Schulz, T.; Torborg, C.; Schäffner, B.; Huang, J.; Zapf, A.; Kadyrov, R.; Börner, A.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 918.
-
[7]
(e) Gallon, B. J.; Kojima, R. W.; Kaner, R. B.; Diaconescu, P. L. Angew. Chem., Int. Ed. 2007, 46, 7251.
-
[8]
(f) Chen, G. S.; Chan, A. S. C.; Kwong, F. Y. Tetrahedron Lett. 2007, 48, 473.
-
[9]
[4] (a) Yang, D. S.; Fu, H. Chem. Eur. J. 2010, 16, 2366.
-
[10]
(b) Kormos, C. M.; Leadbeater, N. E. Tetrahedron 2006, 62, 4728;
-
[11]
(c) Tlili, A.; Xia, N.; Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 8725.
-
[12]
(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.
-
[13]
[5] Yin, L.; Leibescher, J. Chem. Rev. 2007, 107, 133.
-
[14]
[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.
-
[15]
[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.
-
[16]
(b) Kundu, D.; Chatterjee, T.; Ranu, B. C. Adv. Synth. Catal. 2013, 355, 2285.
-
[17]
(c) Brahmachari, G.; Laskar, S.; Barik, P. RSC Adv. 2013, 3, 142;
-
[18]
(d) Parella, R.; Kumar, A; Babu, S. A. Tetrahedron Lett. 2013, 54, 1738.
-
[19]
(e) Yang, S.; Wu, C.; Zhou, H.; Yang, Y.; Zhao, Y.; Wang, C.; Yang, W.; Xu, J. Adv. Synth. Catal. 2013, 355, 53.
-
[20]
(f) Swapna, K.; Murthy, S. N.; Jyothi, M. T.; Nageswar, Y. V. D. Org. Biomol. Chem. 2011, 5989.
-
[21]
(g) Hudson, R.; Ishikawa, S.; Li, C.-J.; Moores, A. Synlett 2013, 1637.
-
[22]
(h) Dandia, A.; Jain, A. K.; Sharma, S. RSC Adv. 2013, 3, 2924.
-
[23]
(i) Kumar, A. S.; Reddy, M.; M.Knorn, A.; Reiser, O.; Sreedhar, B. Eur. J. Org. Chem. 2013, 4, 674.
-
[24]
(j) Wang, Z. L. RSC Adv. 2015, 5, 5563.
-
[25]
[8] Zhang, J.; Han, D.; Zhang, H.; Chaker, M.; Zhao, Y.; Ma, D. Chem. Commun. 2012, 48, 11510.
-
[26]
[9] (a) Makhubela, B. C. E.; Jardine, A.; Smith, G. S. Appl. Catal. 2011, 393, 231.
-
[27]
(b) Lasri, J.; Leod, T. C. O. M.; Pombeiro, A. J. L. Appl. Catal. 2011, 393, 94.
-
[28]
(c) Yi, S. S.; Lee, D. H.; Sin, E.; Lee, Y. S. Tetrahedron Lett. 2007, 48, 6771.
-
[29]
[10] (a) Shen, C.; Xu, J.; Yu, W.; Zhang, P. Green Chem. 2014, 16, 3007.
-
[30]
(b) Shen, C.; Xu, J.; Yu, W. B.; Zhang, P. F. Green Chem. 2014, 16, 3007.
-
[31]
[11] Yang, B.; Mao, Z. X.; Zhu, X. H.; Wan, Y. Q. Catal. Commun. 2015, 60, 92.
-
[32]
[12] Pal, M.; Parasuraman, K.; Yeleswarapu, K. R. Org. Lett. 2003, 5, 349.
-
[33]
[13] Molander, G. A.; Cavalcanti, L. N. J. Org. Chem. 2011, 76, 623.
-
[34]
[14] Jiang, M.; Yang, H. J.; Li, Y.; Jia, Z. Y.; Fu, H. Chin. Chem. Lett. 2014, 25, 715.
-
[35]
[15] Yang, D. S.; An, B. J.; Wei, W.; Jiang, M.; You, J. M.; Wang, H. Tetrahedron 2014, 70, 3630.
-
[36]
[16] Xu, J. M.; Wang, X. Y.; Shao, C. W.; Su, D. Y.; Cheng, G. L.; Hu, Y. F. Org. Lett. 2010, 12, 164.
-
[37]
[17] Tlili, A.; Xia, N.; Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 8725.
-
[1]
-
-
-
[1]
Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
-
[2]
Xi YANG , Chunxiang CHANG , Yingpeng XIE , Yang LI , Yuhui CHEN , Borao WANG , Ludong YI , Zhonghao HAN . Co-catalyst Ni3N supported Al-doped SrTiO3: Synthesis and application to hydrogen evolution from photocatalytic water splitting. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 440-452. doi: 10.11862/CJIC.20240371
-
[3]
Zhanggui DUAN , Yi PEI , Shanshan ZHENG , Zhaoyang WANG , Yongguang WANG , Junjie WANG , Yang HU , Chunxin LÜ , Wei ZHONG . Preparation of UiO-66-NH2 supported copper catalyst and its catalytic activity on alcohol oxidation. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 496-506. doi: 10.11862/CJIC.20230317
-
[4]
Qingqing SHEN , Xiangbowen DU , Kaicheng QIAN , Zhikang JIN , Zheng FANG , Tong WEI , Renhong LI . Self-supporting Cu/α-FeOOH/foam nickel composite catalyst for efficient hydrogen production by coupling methanol oxidation and water electrolysis. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1953-1964. doi: 10.11862/CJIC.20240028
-
[5]
Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-. doi: 10.3866/PKU.WHXB202309027
-
[6]
Zhiquan Zhang , Baker Rhimi , Zheyang Liu , Min Zhou , Guowei Deng , Wei Wei , Liang Mao , Huaming Li , Zhifeng Jiang . Insights into the Development of Copper-based Photocatalysts for CO2 Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2406029-. doi: 10.3866/PKU.WHXB202406029
-
[7]
Qiuyang LUO , Xiaoning TANG , Shu XIA , Junnan LIU , Xingfu YANG , Jie LEI . Application of a densely hydrophobic copper metal layer in-situ prepared with organic solvents for protecting zinc anodes. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1243-1253. doi: 10.11862/CJIC.20240110
-
[8]
Zelong LIANG , Shijia QIN , Pengfei GUO , Hang XU , Bin ZHAO . Synthesis and electrocatalytic CO2 reduction performance of metal-organic framework catalysts loaded with silver particles. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 165-173. doi: 10.11862/CJIC.20240409
-
[9]
Hailang JIA , Hongcheng LI , Pengcheng JI , Yang TENG , Mingyun GUAN . Preparation and performance of N-doped carbon nanotubes composite Co3O4 as oxygen reduction reaction electrocatalysts. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 693-700. doi: 10.11862/CJIC.20230402
-
[10]
Jiapei Zou , Junyang Zhang , Xuming Wu , Cong Wei , Simin Fang , Yuxi Wang . A Comprehensive Experiment Based on Electrocatalytic Nitrate Reduction into Ammonia: Synthesis, Characterization, Performance Exploration, and Applicable Design of Copper-based Catalysts. University Chemistry, 2024, 39(6): 373-382. doi: 10.3866/PKU.DXHX202312081
-
[11]
Xue Dong , Xiaofu Sun , Shuaiqiang Jia , Shitao Han , Dawei Zhou , Ting Yao , Min Wang , Minghui Fang , Haihong Wu , Buxing Han . 碳修饰的铜催化剂实现安培级电流电化学还原CO2制C2+产物. Acta Physico-Chimica Sinica, 2025, 41(3): 2404012-. doi: 10.3866/PKU.WHXB202404012
-
[12]
Kai CHEN , Fengshun WU , Shun XIAO , Jinbao ZHANG , Lihua ZHU . PtRu/nitrogen-doped carbon for electrocatalytic methanol oxidation and hydrogen evolution by water electrolysis. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1357-1367. doi: 10.11862/CJIC.20230350
-
[13]
Xuejiao Wang , Suiying Dong , Kezhen Qi , Vadim Popkov , Xianglin Xiang . Photocatalytic CO2 Reduction by Modified g-C3N4. Acta Physico-Chimica Sinica, 2024, 40(12): 2408005-. doi: 10.3866/PKU.WHXB202408005
-
[14]
Dong-Bing Cheng , Junxin Duan , Haiyu Gao . Experimental Teaching Design on Chitosan Extraction and Preparation of Antibacterial Gel. University Chemistry, 2024, 39(2): 330-339. doi: 10.3866/PKU.DXHX202308053
-
[15]
Jingyu Cai , Xiaoyu Miao , Yulai Zhao , Longqiang Xiao . Exploratory Teaching Experiment Design of FeOOH-RGO Aerogel for Photocatalytic Benzene to Phenol. University Chemistry, 2024, 39(4): 169-177. doi: 10.3866/PKU.DXHX202311028
-
[16]
Yuena Yang , Xufang Hu , Yushan Liu , Yaya Kuang , Jian Ling , Qiue Cao , Chuanhua Zhou . The Realm of Smart Hydrogels. University Chemistry, 2024, 39(5): 172-183. doi: 10.3866/PKU.DXHX202310125
-
[17]
Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
-
[18]
Wenlong LI , Xinyu JIA , Jie LING , Mengdan MA , Anning ZHOU . Photothermal catalytic CO2 hydrogenation over a Mg-doped In2O3-x catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 919-929. doi: 10.11862/CJIC.20230421
-
[19]
Kun WANG , Wenrui LIU , Peng JIANG , Yuhang SONG , Lihua CHEN , Zhao DENG . Hierarchical hollow structured BiOBr-Pt catalysts for photocatalytic CO2 reduction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1270-1278. doi: 10.11862/CJIC.20240037
-
[20]
Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(851)
- HTML views(128)