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

Tianjin Key Laboratory of Structure and Performance for Functional Molecules, Key Laboratory of Inorganic-Organic Hybrid Functional Materials Chemistry, Ministry of Education, College of Chemistry, Tianjin Normal University, Tianjin 300387

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.
- bromodimethylsufonium bromide (BMDS),
- difurylarylmethane,
- synthesis
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.
1. [1]
  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
2. [2]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia 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
3. [3]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang 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
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  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
8. [8]
  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
9. [9]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng 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
10. [10]
  Jianding LI , Junyang FENG , Huimin REN , Gang 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
11. [11]
  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
12. [12]
  Min LIU , Huapeng RUAN , Zhongtao FENG , Xue DONG , Haiyan CUI , Xinping WANG . Neutral boron-containing radical dimers. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 123-130. doi: 10.11862/CJIC.20240362
13. [13]
  Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001
14. [14]
  Yuhao SUN , Qingzhe DONG , Lei ZHAO , Xiaodan JIANG , Hailing GUO , Xianglong MENG , Yongmei GUO . Synthesis and antibacterial properties of silver-loaded sod-based zeolite. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 761-770. doi: 10.11862/CJIC.20230169
15. [15]
  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
16. [16]
  Chengqian Mao , Yanghan Chen , Haotong Bai , Junru Huang , Junpeng Zhuang . Photodimerization of Styrylpyridinium Salt and Its Application in Silk Screen Printing. University Chemistry, 2024, 39(5): 354-362. doi: 10.3866/PKU.DXHX202312014
17. [17]
  Huayan Liu , Yifei Chen , Mengzhao Yang , Jiajun Gu . Strategies for enhancing capacity and rate performance of two-dimensional material-based supercapacitors. Acta Physico-Chimica Sinica, 2025, 41(6): 100063-. doi: 10.1016/j.actphy.2025.100063
18. [18]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
19. [19]
  Tingting Yu , Si Chen , Lianglong Sun , Tongtong Shi , Kai Sun , Xin Wang . Comprehensive Experimental Design for the Photochemical Synthesis, Analysis, and Characterization of Difluoropyrroles. University Chemistry, 2024, 39(11): 196-203. doi: 10.3866/PKU.DXHX202401022
20. [20]
  Yuanyuan Ping , Wangqing Kong . 光催化碳氢键官能团化合成1-苯基-1,2-乙二醇. University Chemistry, 2025, 40(6): 238-247. doi: 10.12461/PKU.DXHX202408092

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(1902)
HTML views(364)

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