Citation: Liu Juyan, Huang Haijing, Jiao Dequan. Synthesis of Difurylarylmethanes Catalyzed by Bromodimethylsulfonium Bromide[J]. Chinese Journal of Organic Chemistry, ;2017, 37(7): 1808-1813. doi: 10.6023/cjoc201612008 shu

Synthesis of Difurylarylmethanes Catalyzed by Bromodimethylsulfonium Bromide

  • Corresponding author: Liu Juyan, hxxyljy@mail.tjnu.edu.cn
  • Received Date: 2 December 2016
    Revised Date: 20 February 2017
    Available Online: 3 July 2017

    Fund Project: Project supported by the Natural Science Foundation of Tianjin City (No. 12JCZDJC34300)the Natural Science Foundation of Tianjin City 12JCZDJC34300

Figures(3)

  • A series of difurylarylmethanes were prepared in high yields by condensation of 2-methylfuran with aromatic aldehydes in the presence of bromodimethylsufonium bromide (BMDS) at room temperature under solvent-free conditions. All products were characterized by 1H NMR and 13C NMR spectra.
  • 加载中
    1. [1]

      (a) Sperry, J. B.; Wright, D. L. Curr. Opin. Drug Discovery Dev. 2005, 8, 723.
      (b) Boto, A.; Alvarez, L. In Heterocycles in Natural Product Synthesis, Wiley-VCH Verlag GmbH & Co. KGaA, 2011, p. 97.
      (c) Ye, O. Z.; Xie, S. X.; Huang, M.; Huang, W. J.; Lu, J. P.; Ma, Z. Q. J. Am. Chem. Soc. 2004, 126, 13940.
      (d)Tan, H. B.; Chen, X. Z.; Liu, Z.; Wang, D. Z. Tetrahedron 2012, 68, 3952.

    2. [2]

      (a) Cui, Z. N.; Shi, Y. X.; Cui, J. R.; Ling, Y.; Li, B. J.; Yang, X. L. Chem. Biol. Drug Des. 2012, 79, 121.
      (b) Iyer, R. S.; Coles, B. F.; Raney, K. D.; Thier, R.; Guengerich, F. P.; Harris, T. M. J. Am. Chem. Soc. 1994, 116, 160.
      (c) Bren, U.; Guengerich, F. P.; Mavri, J. Chem. Res. Toxicol. 2007, 20, 1134.
      (d) Jubert, C.; Mata, J.; Bench, G.; Dashwood, R.; Pereira, C.; Tracewell, W.; Turteltaub, K.; Williams, D.; Bailey, G. Cancer Prev. Res. 2009, 2, 1015.

    3. [3]

      (a) Li, B. L. Chin. J. Org. Chem. 2015, 35, 2487.
      (b) Pan, X. X.; Huo, L. J. Chin. J. Org. Chem. 2016, 36, 687

    4. [4]

      (a) Rodricks, J. V. J. Agric. Food Chem. 1969, 17, 457.
      (b) Lee, N. A.; Wang, S.; Allan, R. D.; Kennedy, I. R. J. Agric. Food Chem. 2004, 52, 2746.

    5. [5]

      (a) Lipshutz, B. H. Chem. Rev. 1986, 86, 795.
      (b) Wong, H. N. C.; Yang, Y. Tetrahedron 1994, 50, 9583.
      (c) Lee, H.-K.; Chan, K.-F.; Hui, C.-W.; Yim, H.-K.; Wu, X.-W.; Wong, H. N. C. Pure Appl. Chem. 2005, 77, 139.

    6. [6]

      (a) Gulevich, A. V.; Dudnik, A. S.; Chernyak, N.; Gevorgyan, V. Chem. Rev. 2013, 113, 3084.
      (b) Keay, B. A. Chem. Soc. Rev. 1999, 28, 209.
      (c) Ma, S. Acc. Chem. Res. 2003, 36, 701.
      (d) Zou, W.; He, Z. R.; He, Z. J. Chin. J. Org. Chem. 2015, 35, 1739.

    7. [7]

      Genovese, S.; Epifano, F.; Pelucchini, C.; Curini, M. Eur. J. Org. Chem. 2009, 2009, 1132.  doi: 10.1002/ejoc.v2009:8

    8. [8]

      (a) Nair, V.; Abhilash, K. G.; Vidya, N. Org. Lett. 2005, 7, 5857.
      (b) Nair, V.; Vidya, N.; Abhilash, K. G. Synthesis 2006, 21, 3647.

    9. [9]

      Chandrasekhar, S.; Khatun, S.; Rajesh, G.; Reddy, Ch. J. Tetrahedron Lett 2009, 50, 669.

    10. [10]

      Qu, H. E.; Xiao, C.; Wang, N.; Yu, K. H.; Hu, Q. S.; Liu, L. X. Molecules 2011, 16, 3855.  doi: 10.3390/molecules16053855

    11. [11]

      Hashmi, A. S. K.; Schwarz, L.; Rubenbauer, P.; Blanco, M. C. Adv. Synth. Catal. 2006, 348, 705.  doi: 10.1002/(ISSN)1615-4169

    12. [12]

      Jaratjaroonphong, J.; Tuengpanya, S.; Saeeng, R.; Udompong, S.; Srisook, K. Eur. J. Med. Chem.. 2014, 83, 561.  doi: 10.1016/j.ejmech.2014.06.045

    13. [13]

      Jaratjaroonphong, J.; Tuengpanya, S.; Ruengsangtongkul, S. J. Org. Chem. 2015, 80, 559.  doi: 10.1021/jo502540k

    14. [14]

      (a) Choudhury, L. H.; Pravin, T.; Khan, A. T. Tetrahedron 2009, 65, 9513.
      (b) Olah, G. A.; Vankar, Y. D.; Arvanaghi, M.; Surya Prakash, G. K. Synthesis 1979, 720.
      (c) Furukawa, N.; Inoue, T.; Aida, T.; Oae, S. J. Chem. Soc., Chem. Commun. 1973, 212a.

    15. [15]

      (a) Choudhury, L. H. Synlett 2006, 1619.
      (b) Khan, A. T.; Ali, A. M.; Goswami, P.; Choudhury, L. H. J. Org. Chem. 2006, 71, 8961.
      (c) Das, B.; Krishnaiah, M.; Katta, V. Tetrahedron Lett. 2006, 47, 4457.
      (d) Khan, A. T.; Mondal, E.; Borah, B. M.; Ghosh, S. Eur. J. Org. Chem. 2003, 4113.
      (e) Khan, A. T.; Islam, S.; Majee, A.; Chattopadhyay, T.; Ghosh, S. J. Mol. Catal., A:Chem. 2005, 239, 158.
      (f) Khan, A. T.; Sahu, P. R.; Majee, A. J. Mol. Catal., A:Chem. 2005, 226, 207.
      (g) Khan, A. T.; Mondal, E.; Ghosh, S.; Islam, S. Eur. J. Org. Chem. 2004, 2002.
      (h) Das, B.; Holla, H.; Srinivas, Y. Tetrahedron Lett. 2007, 48, 61.

    16. [16]

      (a) Zhao, C. Y.; Liu, J. Y.; Wang, Y.; Zhao, X. J.; Yuan, B.; Yue, M. M. Synth. Commun. 2014, 44, 827.
      (b) Yue, M. M.; Liu, J. Y.; Wang, Y.; Yuan, B. Chin. J. Org. Chem. 2014, 34, 190.
      (c) Zhang, L. J.; Liu, J. Y.; Wang, Y.; Chin. J. Org. Chem. 2013, 33, 339.
      (d) Huang, H. J.; Liu, J. Y.; Ma, E. Z.; Cao, Y. Y. Chin. J. Org. Chem. 2015, 35, 2372.

  • 加载中
    1. [1]

      Lifang HEWenjie TANGYaoze LUOMingsheng LIANGJianxin TANGYuxuan WUFuxing ZHANGXiaoming ZHU . Synthesis, structure, and anticancer activity of two dialkyltin complexes constructed based on 2, 2′-bipyridin-6, 6′-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1601-1609. doi: 10.11862/CJIC.20250012

    2. [2]

      Chunling QinShuang ChenHassanien GomaaMohamed A. ShenashenSherif A. El-SaftyQian LiuCuihua AnXijun LiuQibo DengNing Hu . Regulating HER and OER Performances of 2D Materials by the External Physical Fields. Acta Physico-Chimica Sinica, 2024, 40(9): 2307059-0. doi: 10.3866/PKU.WHXB202307059

    3. [3]

      Xiaoyang Li Xiaowei Huang Yimeng Zhang Huan Liu Shao Jin Junpeng Zhuang . Comprehensive Chemical Experiments on the Synthesis of 1,3-Dibromo-5,5-Dimethylhydantoin and Its Application as a Brominating Reagent. University Chemistry, 2025, 40(7): 286-293. doi: 10.12461/PKU.DXHX202408035

    4. [4]

      Jing WUPuzhen HUIHuilin ZHENGPingchuan YUANChunfei WANGHui WANGXiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278

    5. [5]

      Xinting XIONGZhiqiang XIONGPanlei XIAOXuliang NIEXiuying SONGXiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145

    6. [6]

      Bin SUNHeyan JIANG . Glucose-modified bis-Schiff bases: Synthesis and bio-activities in Alzheimer′s disease therapy. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1338-1350. doi: 10.11862/CJIC.20240428

    7. [7]

      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

    8. [8]

      Xinyi ZhangKai RenYanning LiuZhenyi GuZhixiong HuangShuohang ZhengXiaotong WangJinzhi GuoIgor V. ZatovskyJunming CaoXinglong Wu . Progress on Entropy Production Engineering for Electrochemical Catalysis. Acta Physico-Chimica Sinica, 2024, 40(7): 2307057-0. doi: 10.3866/PKU.WHXB202307057

    9. [9]

      Lei FengZe-Min ZhuYing YangZongbin HeJiafeng ZouMan-Bo LiYan ZhaoZhikun Wu . Long-Pursued Structure of Au23(S-Adm)16 and the Unexpected Doping Effects. Acta Physico-Chimica Sinica, 2024, 40(5): 2305029-0. doi: 10.3866/PKU.WHXB202305029

    10. [10]

      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

    11. [11]

      Nan Xiao Fang Sun . 二芳基硫醚化合物的构建及应用. University Chemistry, 2025, 40(6): 360-363. doi: 10.12461/PKU.DXHX202407099

    12. [12]

      Jinyao Du Xingchao Zang Ningning Xu Yongjun Liu Weisi Guo . Electrochemical Thiocyanation of 4-Bromoethylbenzene. University Chemistry, 2024, 39(6): 312-317. doi: 10.3866/PKU.DXHX202310039

    13. [13]

      Yinwu Su Xuanwen Zheng Jianghui Du Boda Li Tao Wang Zhiyan Huang . Green Synthesis of 1,3-Dibromoacetone Using Halogen Exchange Method: Recommending a Basic Organic Synthesis Teaching Experiment. University Chemistry, 2024, 39(5): 307-314. doi: 10.3866/PKU.DXHX202311092

    14. [14]

      Xiaoling LUOPintian ZOUXiaoyan WANGZheng LIUXiangfei KONGQun TANGSheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271

    15. [15]

      Jianding LIJunyang FENGHuimin RENGang LI . Proton conductive properties of a Hf(Ⅳ)-based metal-organic framework built by 2,5-dibromophenyl-4,6-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1094-1100. doi: 10.11862/CJIC.20240464

    16. [16]

      Lili Jiang Shaoyu Zheng Xuejiao Liu Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004

    17. [17]

      Liping GUO . Synthesis and crystal structure characterization of yttrium imido complex: The reactivity of 2-substituted-1-amino-o-carborane with yttrium dialkyl complex. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1409-1415. doi: 10.11862/CJIC.20250065

    18. [18]

      Min LIUHuapeng RUANZhongtao FENGXue DONGHaiyan CUIXinping WANG . Neutral boron-containing radical dimers. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 123-130. doi: 10.11862/CJIC.20240362

    19. [19]

      Mengyang LIHao XUZhonghao NIUChunhua GONGWeihui ZHONGJingli XIE . Highly effective catalytic synthesis of β-amino alcohols by using viologen-polyoxometalate hybrid materials. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1294-1300. doi: 10.11862/CJIC.20250080

    20. [20]

      Kexin Feng Jie Zhang Yujia Sun Qiong Ai Longchun Li . 乙酰二茂铁和二茂铁甲酰丙酮的合成、纯化及表征. University Chemistry, 2025, 40(8): 307-314. doi: 10.12461/PKU.DXHX202409045

Metrics
  • PDF Downloads(1)
  • Abstract views(1938)
  • HTML views(365)

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