A Convenient Access to 3-Substituted Benzofuran Derivatives via Palladium Nanoparticles-Catalyzed Intramolecular Heck Reaction
- Corresponding author: Wang Wei, wangwei1987@cwnu.edu.cn
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
(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./
(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.
(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.
Radadiya, A.; Shah, A. Eur. J. Med. Chem. 2015, 97, 356.
doi: 10.1016/j.ejmech.2015.01.021
(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.
Stipanovic, R. D.; Bell, A. A.; Howell, C. R. Phytochemistry 1975, 14, 1809.
doi: 10.1016/0031-9422(75)85299-X
(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.
Chen, Y.; Wei, X.; Xie, H.; Deng, H. J. Nat. Prod. 2008, 71, 929.
doi: 10.1021/np800016e
(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.
Findlay, J. A.; Buthelezi, S.; Li, G.; Seveck, M.; Miller, J. D. J. Nat. Prod. 1997, 60, 1214.
doi: 10.1021/np970222j
(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.
(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.
(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.
Pei, T.; Chen, C.-Y.; DiMichele, L.; Davies, I. W. Org. Lett. 2010, 12, 4972.
doi: 10.1021/ol102123u
(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.
Wang, S.-H.; Li, P.-H.; Yu, L.; Wang, L. Org. Lett. 2011, 13, 5968.
doi: 10.1021/ol202383z
Liu, L.; Ji, X.; Dong, J.; Zhou, Y.; Yin, S.-F. Org. Lett. 2016, 18, 3138.
doi: 10.1021/acs.orglett.6b01352
Deight, T. A.; Rue, N. R.; Charyk, D.; Josselyn, R.; DeBoef, B. Org. Lett. 2007, 9, 3137.
doi: 10.1021/ol071308z
Theunissen, C.; Wang, J.-J.; Evano, G. Chem. Sci. 2017, 8, 3465.
doi: 10.1039/C6SC05622A
Xu, G.-Y.; Liu, K.; Sun, J.-T. Org. Lett. 2018, 20, 72.
doi: 10.1021/acs.orglett.7b03390
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
Torigoe, T.; Ohmura, T.; Suginome, M. Chem. Eur. J. 2016, 22, 10415.
doi: 10.1002/chem.201602152
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
(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.
(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.
Cho, B. S.; Chung, Y. K. J. Org. Chem. 2017, 82, 2237.
doi: 10.1021/acs.joc.6b02864
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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