Citation: Huang Jin, Fu Ronghui, Jing Linhai, Qin Dabin, Huang Kun, Wang Wei. A Convenient Access to 3-Substituted Benzofuran Derivatives via Palladium Nanoparticles-Catalyzed Intramolecular Heck Reaction[J]. Chinese Journal of Organic Chemistry, ;2019, 39(2): 456-462. doi: 10.6023/cjoc201807040 shu

A Convenient Access to 3-Substituted Benzofuran Derivatives via Palladium Nanoparticles-Catalyzed Intramolecular Heck Reaction

Chemical Synthesis Pollution Control Key Laboratory of Sichuan Province, Institute of Applied Chemistry, College of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002

Corresponding author: Wang Wei, wangwei1987@cwnu.edu.cn
Received Date: 23 July 2018
Revised Date: 29 August 2018
Available Online: 17 February 2018
Fund Project: the Science and Technology Program of Sichuan Province 2018JY0485the National Natural Science Foundation of China 21602144Project supported by the National Natural Science Foundation of China (No. 21602144), and the Science and Technology Program of Sichuan Province (No. 2018JY0485)

Figures(2)

A concise and efficiently route for the synthesis of 3-substituted benzofurans via the intramolecular Heck reaction of bromoaryl 3-phenylallyl ethers has been developed. This simple and highly efficient palladium nanoparticles-catalyzed system showed good catalytic activity. The desired products were affored in good to high yields (45%~96%).
- benzofuran,
- intramolecular Heck reaction,
- palladium nanoparticles
1. [1]
  (a) Lin, Y.-L.; Tsai, Y.-L.; Kuo, Y.-H.; Liu, Y.-H.; Shiao, M.-S. J. Nat. Prod. 1999, 62, 1500.
  (b) Boto, A.; Alvarez, L. Heterocycles in Natural Product Synthesis, Wiley-VCH, Weinheim, Germany, 2011, pp. 97~152.
  (c) La Clair, J. J.; Rheingold, A. L.; Burkart, M. D. J. Nat. Prod. 2011, 74, 2045.
  (d) Simonetti, S. O.; Larghi, E. L.; Bracca, A. B. J.; Kaufman, T. S. Nat. Prod. Rep. 2013, 30, 941./
2. [2]
  (a) Flynn, B. L.; Hamel, E.; Jung, M. K. J. Med. Chem. 2002, 45, 2670.
  (b) Carlsson, B.; Singh, B. N.; Temciuc, M.; Nilsson, S.; Li, Y. L.; Mellin, C.; Malm, J. J. Med. Chem. 2002, 45, 623.
  (c) Cacchi, S.; Fabrizi, G.; Goggiamani, A. Curr. Org. Chem. 2006, 10, 1423.
  (d) Kirilmis, C.; Ahmedzade, M.; Servi, S.; Koca, M.; Kizirgil, A.; Kazaz, C. Eur. J. Med. Chem. 2008, 43, 300.
3. [3]
4. [4]
  (a) Ziegert, R. E.; Toräng, J.; Knepper, K.; Bräse, S. J. Comb. Chem. 2005, 7, 147.
  (b) Tsuji, H.; Mitsui, C.; Ilies, L.; Sato, Y.; Nakamura, E. J. Am. Chem. Soc. 2007, 129, 11902.
  (c) Walker, B.; Tamayo, A. B.; Dang, X. D.; Seo, J. H.; Garcia, A.; Tantiwiwat, M.; Nguyen, T. Q. Adv. Funct. Mater. 2009, 19, 3063.
  (d) Zhang, P.; Yang, Y.-W.; Zheng, X.-L.; Huang, W. H.; Ma, Z.; Shen, Z. R. Chem. Pharm. Bull. 2012, 60, 270.
  (e) Aiken, S.; Allsopp, B.; Booth, K.; Gabbutt, C. D.; Heron, B. M.; Rice, C. R. Tetrahedron 2014, 70, 9352.
5. [5]
  Radadiya, A.; Shah, A. Eur. J. Med. Chem. 2015, 97, 356. doi: 10.1016/j.ejmech.2015.01.021
6. [6]
  (a) Itokawa, H.; Ibraheim, Z. Z.; Qiao, Y. F.; Takeya K. Chem. Pharm. Bull. 1993, 41, 1869.
  (b) Lee, K.-H.; Huang, B.-R. Eur. J. Med. Chem. 2002, 37, 333.
  (c) Lumb, J.-P.; Trauner, D. J. Am. Chem. Soc. 2005, 127, 2870.
  (d) Srivastava, V.; Negi, A. S.; Kumar, J. K.; Faridi, U.; Darokar, M. P.; Luqman, S.; Khanuja, S. P. S. Bioorg. Med. Chem. Lett. 2006, 16, 911.
7. [7]
  Stipanovic, R. D.; Bell, A. A.; Howell, C. R. Phytochemistry 1975, 14, 1809. doi: 10.1016/0031-9422(75)85299-X
8. [8]
  (a) Doe, M.; Shibue, T.; Haraguchi, H.; Morimoto, Y. Org. Lett. 2005, 7, 1765.
  (b) Kapche, G. D. W. F.; Fozing, C. D.; Donfack, J. H.; Fotso, G. W.; Amadou, D.; Tchana, A. N.; Bezabih, M.; Moundipa, P. F.; Ngadjui, B. T.; Abegaz, B. M. Phytochemistry 2009, 70, 216.
  (c) Buckingham, J.; Ranjit, V.; Munasinghe, N. Dictionary of Flavonoids, Taylor and Francis Group, Boca Raton, 2015.
9. [9]
  Chen, Y.; Wei, X.; Xie, H.; Deng, H. J. Nat. Prod. 2008, 71, 929. doi: 10.1021/np800016e
10. [10]
  (a) Wang, L.-Q.; Zhao, Y.-X.; Hu, J. M.; Jia, A.-Q.; Zhou, J. Helv. Chim. Acta 2008, 91, 159.
  (b) Liu, W.; Jiang, X.; Zhang, W.; Jiang, F.; Fu, L. Org. Chem. Curr. Res. 2016, 5, 1000164.
11. [11]
  Findlay, J. A.; Buthelezi, S.; Li, G.; Seveck, M.; Miller, J. D. J. Nat. Prod. 1997, 60, 1214. doi: 10.1021/np970222j
12. [12]
  (a) Guo, X.; Yu, R.; Li, H.; Li, Z. J. Am. Chem. Soc. 2009, 131, 17387.
  (b) Kundu, D.; Samim, M.; Majee A.; Hajra, A. Chem.-Asian J. 2011, 6, 406.
  (c) Ackermann, L.; Kaspar, L. T. J. Org. Chem. 2007, 72, 6149.
13. [13]
  (a) Willis, M. C.; Taylor D.; Gillmore, A. T. Org. Lett. 2004, 6, 4755.
  (b) Anderson, K. W.; Ikawa, T.; Tundel, R. E.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 10694.
  (c) Markina, N. A.; Chen Y.; Larock, R. C. Tetrahedron 2013, 69, 2701.
14. [14]
  (a) Ichake, S. S.; Konala, A.; Kavala, V.; Kuo, C.-W.; Yao, C.-F. Org. Lett. 2017, 19, 54.
  (b) Lee, J. H.; Kim, M.; Kim, I. J. Org. Chem. 2014, 79, 6153.
  (c) Agasti, S.; Dey, A.; Maiti, D. Chem. Commun. 2017, 53, 6544.
15. [15]
  Pei, T.; Chen, C.-Y.; DiMichele, L.; Davies, I. W. Org. Lett. 2010, 12, 4972. doi: 10.1021/ol102123u
16. [16]
  (a) Sharma, U.; Naveen, T.; Maji, A.; Manna, S.; Maiti, D. Angew. Chem., Int. Ed. 2013, 52, 12669.
  (b) Agasti, S.; Sharma, U.; Naveen, T.; Maiti, D. Chem. Commun. 2015, 51, 5375.
17. [17]
  Wang, S.-H.; Li, P.-H.; Yu, L.; Wang, L. Org. Lett. 2011, 13, 5968. doi: 10.1021/ol202383z
18. [18]
  Liu, L.; Ji, X.; Dong, J.; Zhou, Y.; Yin, S.-F. Org. Lett. 2016, 18, 3138. doi: 10.1021/acs.orglett.6b01352
19. [19]
  Deight, T. A.; Rue, N. R.; Charyk, D.; Josselyn, R.; DeBoef, B. Org. Lett. 2007, 9, 3137. doi: 10.1021/ol071308z
20. [20]
  Theunissen, C.; Wang, J.-J.; Evano, G. Chem. Sci. 2017, 8, 3465. doi: 10.1039/C6SC05622A
21. [21]
  Xu, G.-Y.; Liu, K.; Sun, J.-T. Org. Lett. 2018, 20, 72. doi: 10.1021/acs.orglett.7b03390
22. [22]
  Gao, Y.; Xiong, W.-F.; Chen, H.-J.; Wu, W.-Q.; Peng, J.-W.; Gao, Y.-L.; Jiang, H.-F. J. Org. Chem. 2015, 80, 7456. doi: 10.1021/acs.joc.5b01024
23. [23]
  Torigoe, T.; Ohmura, T.; Suginome, M. Chem. Eur. J. 2016, 22, 10415. doi: 10.1002/chem.201602152
24. [24]
  Zhou, R.; Wang, W.; Jiang, Z.-J.; Wang, K.; Zheng, X.-L.; Fu, H.-Y.; Chen, H.; Li, R.-X. Chem. Commun. 2014, 50, 6023. doi: 10.1039/C4CC00815D
25. [25]
  (a) Wang, W.; Yang, Q.; Zhou, R.; Fu, H.-Y.; Chen, H.; Li, R.-X.; Li, X.-J. J. Organomet. Chem. 2012, 697, 1.
  (b) Wang, W.; Zhou, R.; Jiang, Z.-J.; Wang, K.; Fu, H.-Y.; Zheng, X.-L.; Chen, H.; Li, R.-X. Adv. Synth. Catal. 2014, 356, 616.
  (c) Wang, W.; Zhou, R.; Jiang, Z.-J.; Wang, X.; Fu, H.-Y.; Zheng, X.-L.; Chen, H.; Li, R.-X. Eur. J. Org. Chem. 2015, 2579.
26. [26]
  (a) Larock, R. C.; Stinn, D. E. Tetrahedron Lett. 1988, 29, 4687.
  (b) Caddick, S.; Kofie, W. Tetrahedron Lett. 2002, 43, 9347.
  (c) Node, M.; Ozeki, M.; Planas, L.; Nakano, M.; Takita, H.; Mori, D.; Tamatani, S.; Kajimoto, T. J. Org. Chem. 2010, 75, 190.
  (d) Zhou, W.; An, G.-H.; Zhang, G.-Q.; Han, J.-L.; Pan, Y. Org. Biomol. Chem. 2011, 9, 5833.
  (e) Yang, H.-L.; Sun, P.; Zhu, Y.; Yan, H.; Lu, L.-H.; Liu, D.-F.; Rong, G.-W.; Mao, J.-Cheng. Catal. Commun. 2013, 38, 21.
  (f) Gu, Z.-Y.; Liu, C.-G.; Wang, S.-Y.; Ji, S.-J. Org. Lett. 2016, 18, 2379.
  (g) Adak, A. K.; Mandal, A.; Manna, S. K.; Mondal, S. K.; Ghosh, D.; Kundu, D.; Samanta, S.; Ray, J. K. Synth. Commun. 2016, 46, 452.
27. [27]
  Cho, B. S.; Chung, Y. K. J. Org. Chem. 2017, 82, 2237. doi: 10.1021/acs.joc.6b02864
28. [28]
  Wang, W.; Huang, J.; Zhou, R.; Jiang, Z.-J.; Fu, H.-Y.; Zheng, X.-L.; Chen, H.; Li, R.-X. Adv. Synth. Catal. 2015, 357, 2442. doi: 10.1002/adsc.v357.11
1. [1]
  Yongming Guo , Jie Li , Chaoyong Liu . Green Improvement and Educational Design in the Synthesis and Characterization of Silver Nanoparticles. University Chemistry, 2024, 39(3): 258-265. doi: 10.3866/PKU.DXHX202309057
2. [2]
  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
3. [3]
  Lina Liu , Xiaolan Wei , Jianqiang Hu . Exploration of Subject-Oriented Undergraduate Comprehensive Chemistry Experimental Teaching Based on the “STS Concept”: Taking the Experiment of Gold Nanoparticles as an Example. University Chemistry, 2024, 39(10): 337-343. doi: 10.12461/PKU.DXHX202405112
4. [4]
  Caixia Lin , Zhaojiang Shi , Yi Yu , Jianfeng Yan , Keyin Ye , Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005
5. [5]
  Weihan Zhang , Menglu Wang , Ankang Jia , Wei Deng , Shuxing Bai . 表面硫物种对钯-硫纳米片加氢性能的影响. Acta Physico-Chimica Sinica, 2024, 40(11): 2309043-. doi: 10.3866/PKU.WHXB202309043
6. [6]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
7. [7]
  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
8. [8]
  Yongzhi LI , Han ZHANG , Gangding WANG , Yanwei SUI , Lei HOU , Yaoyu WANG . A two-dimensional metal-organic framework for the determination of nitrofurantoin and nitrofurazone in aqueous solution. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 245-253. doi: 10.11862/CJIC.20240307
9. [9]
  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
10. [10]
  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
11. [11]
  Yu Dai , Xueting Sun , Haoyu Wu , Naizhu Li , Guoe Cheng , Xiaojin Zhang , Fan Xia . Determination of the Michaelis Constant for Gold Nanozyme-Catalyzed Decomposition of Hydrogen Peroxide. University Chemistry, 2025, 40(5): 351-356. doi: 10.12461/PKU.DXHX202407052
12. [12]
  Xuhui Fan , Fan Wang , Mengjiao Li , Faiza Meharban , Yaying Li , Yuanyuan Cui , Xiaopeng Li , Jingsan Xu , Qi Xiao , Wei Luo . Visible light excitation on CuPd/TiN with enhanced chemisorption for catalyzing Heck reaction. Chinese Chemical Letters, 2025, 36(1): 110299-. doi: 10.1016/j.cclet.2024.110299
13. [13]
  Jiaxun Wu , Mingde Li , Li Dang . The R eaction of Metal Selenium Complexes with Olefins as a Tutorial Case Study for Analyzing Molecular Orbital Interaction Modes. University Chemistry, 2025, 40(3): 108-115. doi: 10.12461/PKU.DXHX202405098
14. [14]
  Yufang GAO , Nan HOU , Yaning LIANG , Ning LI , Yanting ZHANG , Zelong LI , Xiaofeng LI . Nano-thin layer MCM-22 zeolite: Synthesis and catalytic properties of trimethylbenzene isomerization reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1079-1087. doi: 10.11862/CJIC.20240036
15. [15]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
16. [16]
  Endong YANG , Haoze TIAN , Ke ZHANG , Yongbing LOU . Efficient oxygen evolution reaction of CuCo₂O₄/NiFe-layered bimetallic hydroxide core-shell nanoflower sphere arrays. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 930-940. doi: 10.11862/CJIC.20230369
17. [17]
  Fanpeng Meng , Fei Zhao , Jingkai Lin , Jinsheng Zhao , Huayang Zhang , Shaobin Wang . 优化氮化碳纳米片/球形共轭聚合物S型异质结界面电场以促进析氢反应. Acta Physico-Chimica Sinica, 2025, 41(8): 100095-. doi: 10.1016/j.actphy.2025.100095
18. [18]
  Dan Liu . 可见光-有机小分子协同催化的不对称自由基反应研究进展. University Chemistry, 2025, 40(6): 118-128. doi: 10.12461/PKU.DXHX202408101
19. [19]
  Ling Liu , Haibin Wang , Genrong Qiang . Curriculum Ideological and Political Design for the Comprehensive Preparation Experiment of Ethyl Benzoate Synthesized from Benzyl Alcohol. University Chemistry, 2024, 39(2): 94-98. doi: 10.3866/PKU.DXHX202304080
20. [20]
  Feng Sha , Xinyan Wu , Ping Hu , Wenqing Zhang , Xiaoyang Luan , Yunfei Ma . Design of Course Ideology and Politics for the Comprehensive Organic Synthesis Experiment of Benzocaine. University Chemistry, 2024, 39(2): 110-115. doi: 10.3866/PKU.DXHX202307082

Get Citation

PDF

XML

Metrics

PDF Downloads(8)
Abstract views(892)
HTML views(122)

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