Citation: Xu Xiuzhi, Zhang Fan, Huang Sheng, Zhang Zhiqiang, Ke Fang. Visible-Light Promoted Hydroxylation of Aryl Halides under Mild Reaction Conditions in Neat Water[J]. Chinese Journal of Organic Chemistry, ;2020, 40(9): 2912-2918. doi: 10.6023/cjoc202005004 shu

Visible-Light Promoted Hydroxylation of Aryl Halides under Mild Reaction Conditions in Neat Water

  • Corresponding author: Xu Xiuzhi, xiuzhi_xu@126.com Ke Fang, kefang612@163.com
  • Received Date: 2 May 2020
    Revised Date: 12 June 2020
    Available Online: 15 July 2020

    Fund Project: the Natural Science Foundation of Fujian Province 2016Y9053the Natural Science Foundation of Fujian Province 2017-1-64the Natural Science Foundation of Fujian Province 2016Y9052Project supported by the Natural Science Foundation of Fujian Province (Nos. 2016Y9052, 2016Y9053, 2017J01820, 2017-1-64)the Natural Science Foundation of Fujian Province 2017J01820

Figures(6)

  • A novel visible-light-introduced reaction for the construction of phenols via hydroxylation of aryl halides has been developed. The reaction has been achieved in high yield under mild conditions by using iodine as photocatalyst, which is cheap, easy to handle and environmentally friendly. A variety of phenols were obtained in up to 92% yields. Moreover, aryl chlorides were also successfully employed as substrates, affording the target phenols in good isolated yields. It might provide promising protocol for the synthesis of phenol derivatives. Its application was performed by the synthesis of 5-acetyl-4-hy-droxy-2-methoxybenzyl diisopropylcarbamodithioate, which displayed significant anti-proliferation effect.
  • 加载中
    1. [1]

      (a) Kwong, H.-K.; Lo, P.-K.; Yiu, S.-M.; Hirao, H.; Lau, K.-C.; Lau, T.-C. Angew. Chem.. Int. Ed. 2017, 56, 12260.
      (b) Bracegirdle, S.; Anderson, E. A. Chem. Commun. 2010, 46, 3454.
      (c) Ohwada, A.; Nara, S.; Sakamoto, T.; Kikugawa, Y. J. Chem. Soc.. Perkin Trans. 12001, 3064.
      (d) Rayment, E. J.; Summerhill, N.; Anderson, E. A. J. Org. Chem. 2012, 77, 7052.
      (e) Morimoto, Y.; Bunno, S.; Fujieda, N.; Sugimoto, H.; Itoh, S. J. Am. Chem. Soc. 2015, 137, 5867.
      (f) Yin, W.; Pan, X.; Leng, W.; Chen, J.; He, H. Green Chem. 2019, 21, 4614.

    2. [2]

      (a) Nakayama, M.; Fukuoka, Y.; Nozaki, H.; Matsuo, A.; Hayashi, S. Chem. Lett. 1980, 9, 1243.
      (b) Rappoport, Z. The Chemistry of Phenols, Wiley, Hoboken, N. J., 2003.

    3. [3]

      (a) Schmidt, R. J. Appl. Catal. A 2005, 280, 89.
      (b) Fyfe, C. A. The Chemistry of the Hydroxyl Group, Vol. 1, Ed.: Patai, S., Wiley-Interscience, New York, 1971, pp. 83~127.

    4. [4]

      Cornils, B.; Herrmann, W. A. J. Catal. 2003, 216, 23.  doi: 10.1016/S0021-9517(02)00128-8

    5. [5]

      Taddei, M.; Ricci, A. Synthesis 1986, 1986, 633.  doi: 10.1055/s-1986-31725

    6. [6]

      (a) Damkaci, F.; Sigindere, C.; Sobiech, T.; Vik, E.; Malone, J. Tetrahedron Lett. 2017, 58, 3559.
      (b) Ding, G.; Han, H.; Jiang, T.; Wu, T.; Han, B. Chem. Commun. 2014, 50, 9072.
      (c) Ghiasbeigi, E.; Soleiman-Beigi, M. ChemistrySelect 2019, 4, 3611.
      (d) Mketo, N.; Jordaan, H. J. L.; Jordaan, A.; Swarts, A. J.; Mapolie, S. F. Eur. J. Inorg. Chem. 2016, 3781.
      (e) Wang, D.; Kuang, D.; Zhang, F.; Tang, S.; Jiang, W. Eur. J. Org. Chem. 2014, 315.
      (f) Xia, S.; Gan, L.; Wang, K.; Li, Z.; Ma, D. J. Am. Chem. Soc. 2016, 138, 13493.
      (g) Shendage, S. S. J. Chem. Sci. 2018, 130, 13.
      (h) Cyr, P.; Charette, A. B. Synlett 2014, 25, 1409.
      (i) Ramu, R.; Wanna, W. H.; Janmanchi, D.; Tsai, Y.-F.; Liu, C.-C.; Mou, C.-Y.; Yu, S.-S. Mol. Catal. 2017, 441, 114.

    7. [7]

      Fier, P. S.; Maloney, K. M. Org. Lett. 2017, 19, 3033.  doi: 10.1021/acs.orglett.7b01403

    8. [8]

      Zhao, P.; Zhang, Y.; Li, D.; Cui, H.; Zhang, L. Chin. J. Catal. 2018, 39, 334.  doi: 10.1016/S1872-2067(17)62991-7

    9. [9]

    10. [10]

    11. [11]

      Jiang, M.; Yang, H.; Fu, H. Org. Lett. 2016, 18, 5248.  doi: 10.1021/acs.orglett.6b02553

    12. [12]

      (a) Zablocka, M.; Hameau, A.; Caminade, A.-M.; Majoral, J.-P. Adv. Synth. Catal. 2010, 352, 2341.
      (b) Zhang, M.; Ruzi, R.; Li, N.; Xie, J.; Zhu, C. Org. Chem. Front. 2018, 5, 749.
      (c) Kitanosono, T.; Masuda, K.; Xu, P.; Kobayashi, S. Chem. Rev. 2018, 118, 679.
      (d) Song, G.-L.; Zhang, Z.; Da, Y.-X.; Wang, X.-C. Tetrahedron 2015, 71, 8823.

    13. [13]

      Jiang, M.; Yang, H.; Fu, H. Org. Lett. 2016, 18, 5248.  doi: 10.1021/acs.orglett.6b02553

    14. [14]

      (a) Ke, F.; Xu, Y.; Zhu, S.; Lin, X.; Lin, C.; Zhou, S.; Su, H. Green Chem. 2019, 21, 4329.
      (b) Ke, F.; Liu, C.; Zhang, P.; Xu, J.; Chen, X. Synth. Commun. 2018, 48, 3089.

    15. [15]

      (a) Tian, Y.-E.; Sun, D.; Han, X.-X.; Yang, J.-M.; Zhang, S.; Feng, N.-N.; Zhu, L.-N.; Xu, Z.-Y.; Che, Z.-P.; Liu, S.-M.; Lin, X.-M.; Jiang, J.; Chen, G.-Q. J. Asian Nat. Prod. Res. 2020, Doi: 10.1080/10286020.2020.1718116.
      (b) Peng, Y.; Zheng, X.; Fan, Z.; Zhou, H.; Zhu, X.; Wang, G.; Liu, Z. Phytomedicine 2020, 68, Article 153151.

    16. [16]

      (a) Cheng, C.-S.; Chen, J.-X; Tang, J.; Geng, Y.-W.; Zheng, L.; Lv, L.-L.; Chen, L.-Y.; Chen, Z. Cancer Manage. Res. 2020, 12, 641.
      (b) Huang, W.; Ding, Y.; Miao, Y.; Liu, M.-Z.; Li, Y.; Yang, G.-F. Eur. J. Med. Chem. 2009, 44, 3687.

    17. [17]

      (a) Cai, Y.-M.; Xu, Y.-T.; Zhang, X. Gao, W.-X.; Huang, X.-B.; Liu, M.-C.; Wu, H.-Y. Org. Lett. 2019, 21, 10169.
      (b) Jung, S.-H.; Yeon, J.-W.; Hong, S. Y.; Kang, Y.; Song, K. Nucl. Sci. Eng. 2015, 181, 191.
      (c) Banerjee, A.; Lei, Z.; Ngal, M.-Y. Synthesis 2019, 51, 303.
      (d) Liu, W.; Li, J.; Huang, C.-Y.; Li, C.-J. Angew. Chem.. Int. Ed. 2020, 59, 1786.
      (e) Li, L.; Liu, W.; Zeng, H.; Mu, X.; Cosa, G.; Mi, Z.; Li, C.-J. J. Am. Chem. Soc. 2015, 137, 8328.

    18. [18]

      (a) González-Calderón, D.; González-González, C.-A.; Fuentes-Benítez, A.; Cuevas-Yáñez, E.; Corona-Becerril, D.; González-Romero, C. Helv. Chim. Acta 2014, 97, 965.
      (b) Bora, S. J.; Chetia, B. J. Organomet. Chem. 2017, 851, 52.
      (c) Reitti, M.; Gurubrahamam, R., Walther, M.; Lindstedt, E.; Olofsson, B. Org. Lett. 2018, 20, 1785.
      (d) Sang, D.; Wang, J.; Zheng, Y.; He, J.; Yuan, C.; An, Q.; Tian, J. Synthesis 2017, 49, 2721.
      (e) Ghorbani-Choghamarani, A.; Goudarziafshar, H.; Nikoorazm, M.; Naseri Z. Chin. Chem. Lett. 2011, 22, 1431.
      (f) Rahimi, J.; Taheri-Ledari, R.; Niksefat, M.; Maleki A. Catal. Commun. 2020, 134, 105850.
      (g) Xu, J.; Wang, X.; Shao, C.; Su, D.; Cheng, G..; Hu, Y. Org. Lett. 2010, 12, 1964.
      (h) Sodhi, R. K.; Paul, S.; Clark, J. H. Green Chem. 2012, 14, 1649.
      (i) Chatterjee, N.; Chowdhury, H.; Sneh, K.; Goswami A. Tetrahedron Lett. 2015, 56, 172.
      (j) Richter, H.; Beckendorf, S.; Mancheño, O. G. Adv. Synth. Catal. 2011, 353, 295.
      (k) Sridhar, A.; Rangasamy, R.; Selvaraj, M. New J. Chem. 2019, 43, 17974.

    19. [19]

      Jing, L.; Wei, J.; Zhou, L.; Li, Z.; Zhou, X. Chem. Commun. 2010, 46, 4767.  doi: 10.1039/c0cc00434k

  • 加载中
    1. [1]

      Shihui Shi Haoyu Li Shaojie Han Yifan Yao Siqi Liu . Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy. University Chemistry, 2024, 39(5): 336-344. doi: 10.3866/PKU.DXHX202312002

    2. [2]

      Bing LIUHuang ZHANGHongliang HANChangwen HUYinglei ZHANG . Visible light degradation of methylene blue from water by triangle Au@TiO2 mesoporous catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 941-952. doi: 10.11862/CJIC.20230398

    3. [3]

      Geyang Song Dong Xue Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030

    4. [4]

      Xinzhe HUANGLihui XUYue YANGLiming WANGZhangyong LIUZhongjian WANG . Preparation and visible light responsive photocatalytic properties of BiSbO4/BiOBr. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 284-292. doi: 10.11862/CJIC.20240212

    5. [5]

      Zhen Yao Bing Lin Youping Tian Tao Li Wenhui Zhang Xiongwei Liu Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033

    6. [6]

      Jie Li Huida Qian Deyang Pan Wenjing Wang Daliang Zhu Zhongxue Fang . Efficient Synthesis of Anethaldehyde Induced by Visible Light. University Chemistry, 2024, 39(4): 343-350. doi: 10.3866/PKU.DXHX202310076

    7. [7]

      Bo YANGGongxuan LÜJiantai MA . Nickel phosphide modified phosphorus doped gallium oxide for visible light photocatalytic water splitting to hydrogen. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 736-750. doi: 10.11862/CJIC.20230346

    8. [8]

      Yurong Tang Yunren Shi Yi Xu Bo Qin Yanqin Xu Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087

    9. [9]

      Qin Li Huihui Zhang Huajun Gu Yuanyuan Cui Ruihua Gao Wei-Lin DaiIn situ Growth of Cd0.5Zn0.5S Nanorods on Ti3C2 MXene Nanosheet for Efficient Visible-Light-Driven Photocatalytic Hydrogen Evolution. Acta Physico-Chimica Sinica, 2025, 41(4): 100031-. doi: 10.3866/PKU.WHXB202402016

    10. [10]

      Hongting Yan Aili Feng Rongxiu Zhu Lei Liu Dongju Zhang . Reexamination of the Iodine-Catalyzed Chlorination Reaction of Chlorobenzene Using Computational Chemistry Methods. University Chemistry, 2025, 40(3): 16-22. doi: 10.12461/PKU.DXHX202403010

    11. [11]

      Yunhao Zhang Yinuo Wang Siran Wang Dazhen Xu . Progress in Selective Construction of Functional Aromatics from Nitrogenous Cycloalkanes. University Chemistry, 2024, 39(11): 136-145. doi: 10.3866/PKU.DXHX202401083

    12. [12]

      Daojuan Cheng Fang Fang . Exploration and Implementation of Science-Education Integration in Organic Chemistry Teaching for Pharmacy Majors: A Case Study on Nucleophilic Substitution Reactions of Alkyl Halides. University Chemistry, 2024, 39(11): 72-78. doi: 10.12461/PKU.DXHX202403105

    13. [13]

      Yanhui Zhong Ran Wang Zian Lin . Analysis of Halogenated Quinone Compounds in Environmental Water by Dispersive Solid-Phase Extraction with Liquid Chromatography-Triple Quadrupole Mass Spectrometry. University Chemistry, 2024, 39(11): 296-303. doi: 10.12461/PKU.DXHX202402017

    14. [14]

      Lin Ding Jinpeng Zhang Junfeng Li Daying Liu . Color Catcher: A Marvelous Encounter of Starch and Iodine. University Chemistry, 2024, 39(6): 334-341. doi: 10.3866/PKU.DXHX202311064

    15. [15]

      Lihui Jiang Wanrong Dong Hua Yang Yongqing Xia Hongjian Peng Jun Yuan Xiaoqian Hu Zihan Zeng Yingping Zou Yiming Luo . Study on Extraction of p-Hydroxyacetophenone. University Chemistry, 2024, 39(11): 259-268. doi: 10.12461/PKU.DXHX202402056

    16. [16]

      Jiarui Wu Gengxin Wu Yan Wang Yingwei Yang . Crystal Engineering Based on Leaning Towerarenes. University Chemistry, 2024, 39(3): 58-62. doi: 10.3866/PKU.DXHX202304014

    17. [17]

      Yi Li Zhaoxiang Cao Peng Liu Xia Wu Dongju Zhang . Revealing the Coloration and Color Change Mechanisms of the Eriochrome Black T Indicator through Computational Chemistry and UV-Visible Absorption Spectroscopy. University Chemistry, 2025, 40(3): 132-139. doi: 10.12461/PKU.DXHX202405154

    18. [18]

      Ruitong Zhang Zhiqiang Zeng Xiaoguang Zhang . Improvement of Ethyl Acetate Saponification Reaction and Iodine Clock Reaction Experiments. University Chemistry, 2024, 39(8): 197-203. doi: 10.3866/PKU.DXHX202312004

    19. [19]

      Chen LUQinlong HONGHaixia ZHANGJian ZHANG . Syntheses, structures, and properties of copper-iodine cluster-based boron imidazolate framework materials. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 149-154. doi: 10.11862/CJIC.20240407

    20. [20]

      Jingke LIUJia CHENYingchao HAN . Nano hydroxyapatite stable suspension system: Preparation and cobalt adsorption performance. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1763-1774. doi: 10.11862/CJIC.20240060

Metrics
  • PDF Downloads(18)
  • Abstract views(1866)
  • HTML views(454)

通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return