Citation: Li Yibiao, Cheng Liang, Chen Lu, Li Bin, Sun Ning, Qing Ning. One-Pot Synthesis of Substituted Thiophene and Furan Derivatives from Terminal Alkynes[J]. Chinese Journal of Organic Chemistry, ;2016, 36(10): 2426-2436. doi: 10.6023/cjoc201603029 shu

One-Pot Synthesis of Substituted Thiophene and Furan Derivatives from Terminal Alkynes

Li Yibiao ^a,*,, ,
Cheng Liang ^a ,
Chen Lu ^a ,
Li Bin ^a ,
Sun Ning ^b ,
Qing Ning ^a

a.
School of Chemical & Environmental Engineering, Wuyi University, Jiangmen 529020
b.
Department of Material Technology, Jiangmen Polytechnic, Jiangmen 529020

Corresponding author: Li Yibiao, leeyib268@126.com
Received Date: 16 March 2016
Revised Date: 17 May 2016

Fund Project: Foundation for Distinguished Young Talents in Higher Education of Guangdong Province 2013LYM_0094Science Foundation for Young Teachers of Wuyi University 2015td01National Natural Science Foundation of China 21302146Natural Science Foundation of Guangdong Province S2013040012354

Figures(3)

The development of efficient and sustainable methods for the synthesis of thiophene and furan derivatives is an important task because of the central role of this class of compounds in many natural products, pharmaceuticals and designed materials applications. In this work, a highly efficient selective synthesis of 2,5-disubstituted furan, 2,5-disubstituted thiophene derivatives, benzo[b]furan and benzo[b]thiophene derivatives using terminal alkynes has been developed. This one-pot procedure involves C(sp)-C(sp) oxidative coupling reaction, the selective hydration and intramolecular annulation of two C≡C triple bond which is a promising synthetic strategy. Meanwhile, the benzo[b]furan and benzo[b]thiophene derivatives were facilely synthesized via Sonogashira coupling reaction, regioselective C-F bond hydration and annulation process in good yield. This reaction was a convenient and simple pathway for the synthesis of the thiophene or furan derivatives.
- one-pot synthesis,
- thiophene,
- furan,
- terminal alkyne
1. [1]
2. [2]
  For selected review, see:(a) Wu, X. F.; Neumann, H.; Beller, M. Chem. Rev. 2013, 113, 1. (b) Zeni, G.; Larock, R. C. Chem. Rev. 2006, 106, 4644. (c) Lipshutz, B. H. Chem. Rev. 1986, 86, 795. (d) Lu, H.; Liu, G. T. Planta Med. 1992, 58, 311. (e) Navarro, E.; Alonso, S. J.; Trujillo, J.; Jorge, E.; Pérez, C. J. Nat. Prod. 2001, 64, 134. (f) Cacchi, S.; Fabrizi, G.; Goggiamani, A. Org. Biomol. Chem. 2011, 9, 641. (g) Flynn, B. L.; Hamel, E.; Jung, M. K. J. Med. Chem. 2002, 45, 2670. (h) Palkowitz, A. D.; Glasebrook, A. L.; Thrasher, K. J.; Hauser, K. L.; Short, L. L.; Philips, D. L.; Muehl, B. S.; Sato, M.; Shetler, P. K.; Cullinan, G. J.; Pell, T. R.; Bryant, H. U. J. Med. Chem. 1997, 40, 1407. (i) Tsuji, H.; Cantagrel, G.; Ueda, Y.; Chen, T.; Wan, L. J.; Nakamura, E. Chem. Asian J. 2013, 8, 2377.
3. [3]
  Li, F.; Chordia, M. D.; Woodling, K. A.; Macdonald, T. L. Chem. Res. Toxicol. 2007, 20, 1854. (b) Carter, G. W.; Young, P. R.; Albert, D. H.; Bouska, J.; Dyer, R.; Bell, L.; Summers J. B.; Brooks, D. W. J. Pharmacol. Exp. Ther. 1991, 256, 929.
4. [4]
  Qin, Z.; Kastrati, I.; Chandrasena, R. E. P.; Liu, H.; Yao, P.; Petukhov, P. A.; Bolton, J. L.; Thatcher, G. R. J. J. Med. Chem. 2007, 50, 2682.
5. [5]
6. [6]
7. [7]
  Lenden, P.; Entwistle, D. A.; Willis, M. C. Angew. Chem., Int. Ed. 2011, 50, 10657. (b) Nun, P.; Dupuy, S.; Gaillard, S.; Poater, A.; Cavallo, L.; Nolan, S. P. Catal. Sci. Technol. 2011, 1, 58. (c) Kel'in, A. V.; Gevorgyan, V. J. Org. Chem. 2002, 67, 95. (d) Rao, H. S. P.; Jothilingam, S. J. Org. Chem. 2003, 68, 5392. (e) Aponick, A.; Li, C. Y.; Malinge, J.; Marques, E. F. Org. Lett. 2009, 11, 4624. (f) Egi, M.; Azechi, K.; Akai, S. Org. Lett. 2009, 11, 5002. (g) Dheur, J.; Sauthier, M.; Castanet, Y.; Mortreux, A. Adv. Synth. Catal. 2010, 352, 557.
8. [8]
  Zheng, Q.; Hua, R.; Jiang, J.; Zhang, L. Tetrahedron 2014, 70, 8252. (b) Zheng, Q.; Hua, R.; Yin, T. Curr. Org. Synth. 2013, 10, 161.
9. [9]
  Klukas, F.; Grunwald, A.; Menschel, F.; Müller, T. J. J. Beilstein J. Org. Chem. 2014, 10, 672.
10. [10]
  Kramer, S.; Madsen, J. L. H.; Rottländer, M.; Skrydstrup, T. Org. Lett. 2010, 12, 2758. (b) Sheng, H. Y.; Lin, S. Y.; Huang, Y. C. Synthesis 1987, 1022.
11. [11]
  Jiang, H.; Zeng, W.; Li, Y.; Wu, W.; Huang, L.; Fu, W. J. Org. Chem. 2012, 77, 5179.
12. [12]
  Zhang, M.; Jiang, H. F.; Neumann, H.; Beller, M.; Dixneuf, P. Angew. Chem., Int. Ed. 2009, 48, 1681.
13. [13]
  Zhang, G.; Yi, H.; Chen, H.; Bian, C.; Liu, C. Lei, A. Org. Lett. 2014, 16, 6156.
14. [14]
  Tang, S.; Liu, K.; Long, Y.; Gao, X.; Gao, M.; Lei, A. Org. Lett. 2015, 17, 2404.
15. [15]
  Karatas, F.; Koca, M.; Kara, H.; Servi, S. Eur. J. Med. Chem. 2006, 41, 664. (b) Navarro, E.; Alonso, S. J.; Trujillo, J.; Jorge, E.; Pérez, C. J. Nat. Prod. 2001, 64, 134. (c) Flynn, B. L.; Hamel, E.; Jung, M. K. J. Med. Chem. 2002, 45, 2670. (d) Lu, H.; Liu, G. T. Planta Med. 1992, 58, 311. (e) Wu, X. F.; Neumann, H.; Beller, M. Chem. Rev. 2013, 113, 1.
16. [16]
  Kraus, G. A.; Schroeder, J. D. Synlett 2005, 2504. (b) Anxionnat, B.; Pardo, D. G.; Ricci, G.; Rossen, K.; Cossy, J. Org. Lett. 2013, 15, 3876. (c) Liang, Z.; Hou, W.; Du, Y.; Zhang, Y.; Pan, Y.; Mao, D.; Zhao, K. Org. Lett. 2009, 11, 4978. (d) Wang, X.; Liu, M.; Xu, L.; Wang, Q.; Chen, J.; Ding, J.; Wu, H. J. Org. Chem. 2013, 78, 5273. (e) Siddiqui, I. R.; Waseem, M. A.; Shamim, S.; Shireen, Srivastava, A.; Srivastava A. Tetrahedron Lett. 2013, 54, 4154.
17. [17]
  Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285. (b) Cho, C. H.; Neuenswander, B.; Lushington, G. H.; Larock, R. C. J. Comb. Chem. 2008, 10, 941.
18. [18]
  Liu, Y.; Wang, H.; Wan, J.-P. J. Org. Chem. 2014, 79, 10599. (b) Wan, J-P.; Wang, H.; Liu, Y.; Ding, H. Org. Lett. 2014, 16, 5160.
19. [19]
  Guilarte, V.; Fernández-Rodríguez, M. A.; García-García, P.; Hernandor, E.; Sanz, R. Org. Lett. 2011, 13, 5100.
20. [20]
  Prasad, D. J. C.; Sekar, G. Org. Biomol. Chem. 2013, 11, 1659.
21. [21]
  Kuhn, M.; Falk, F. C.; Paradies, J. Org. Lett. 2011, 13, 4100.
22. [22]
  Li, Y.; Cheng, L.; Liu, X.; Li, B.; Sun, N. Beilstein J. Org. Chem. 2014, 10, 2886.
23. [23]
  Ackermann, L.; Kaspar, L. T. J. Org. Chem. 2007, 72, 6149.
24. [24]
  Sun, L. L.; Deng, C. L.; Tang, R. Y.; Zhang, X. G. J. Org. Chem. 2011, 76, 7546. (b) Ma, D.; Xie, S.; Xue, P.; Zhang, X.; Dong, J.; Jiang, Y. Angew. Chem., Int. Ed. 2009, 48, 4222.
25. [25]
  Irudayanathan, F. M.; Raja, G. C. E.; Lee, S. Tetrahedron 2015, 71, 4418.
26. [26]
  Urselmann, D.; Antovic, D.; Müller, T. J. J. Beilstein J. Org. Chem. 2011, 7, 1499.
27. [27]
  Tan, J.; Zhao, X. RSC Adv. 2012, 2, 5488.
28. [28]
  Moure, M. J.; Martin, R. S.; Domínguez, E. Adv. Synth. Catal. 2014, 356, 2070.
29. [29]
  Rao, M. L. N.; Awasthi, D. K.; Talode, J. B. Tetrahedron Lett. 2012, 53, 2662.
30. [30]
  Dao-Huy, T.; Haider, M.; Clatz, F.; Schnürch, M.; Mihovilovic, M. D. Eur. J. Org. Chem. 2014, 8119.
31. [31]
  Jaseer, E. A.; Prasad, D. J. C.; Sekar, G. Tetrahedron 2010, 66, 2077.
32. [32]
  Duan, X. F.; Zeng, J.; Zhang, Z. B.; Zi, G. F. J. Org. Chem. 2007, 72, 10283.
33. [33]
  Pan, W. B.; Chen, C. C.; Wei, L. L.; Wei, L. M.; Wu, M. M. Tetrahedron Lett. 2013, 54, 2655.
34. [34]
  Bryan, C. S.; Braunger, J. A.; Lautens, M. Angew. Chem., Int. Ed. 2009, 48, 7064.
35. [35]
  Bíró, A. B.; Kotschy, A. Eur. J. Org. Chem. 2007, 1364.
36. [36]
  Li, Y.; Cheng, L.; Li, B.; Jiang, S.; Chen, L.; Shao, Y. Chem. Select. 2016, 1, 1092.
1. [1]
  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
2. [2]
  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
3. [3]
  Xinxin Dai , Di Lan , Xingliang Chen , Xingwei Wang , Guangbin Ji . One pot green synthesis and electromagnetic wave absorption performance of manganese dioxide@nitrogen-doped carbon@NiFe₂O₄ hybrids. Acta Physico-Chimica Sinica, 2026, 42(8): 100302-0. doi: 10.1016/j.actphy.2026.100302
4. [4]
  Mengyang LI , Zhonghao NIU , Hao XU , Jingli XIE . One-pot synthesis of 4H-pyran derivatives catalyzed by viologen-modified metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2026, 42(7): 1513-1522. doi: 10.11862/CJIC.20250205
5. [5]
  Haolin Yang , Aoxiang Fan , Yi Song , Yang Chen . 基于甲酰化-共轭脱氢串联策略的苯并呋喃-5-甲醛的制备——推荐一个基础有机合成综合性教学实验. University Chemistry, 2026, 41(5): 141-148. doi: 10.12461/PKU.DXHX202511156
6. [6]
  Feng LI , Shujuan GAO . One-step preparation and energy storage properties of MXene-doped poly(3, 4-ethylenedioxythiophene) composite electrodes. Chinese Journal of Inorganic Chemistry, 2026, 42(7): 1485-1494. doi: 10.11862/CJIC.20260019
7. [7]
  Xiaoqi LAN , Wei LI , Long JING , Mengyu SU , Xiaoling LUO , Zheng LIU , Qun TANG . Synthesis, crystal structure, and spectral properties of transition-metal-organic frameworks based on thiophene carboxylic acid ligands. Chinese Journal of Inorganic Chemistry, 2026, 42(2): 309-316. doi: 10.11862/CJIC.20250212
8. [8]
  Yukun Chang , Haoqin Huang , Baolei Wang . Preparation of Trans-Cinnamic Acid via “One-Pot” Protocol of Aldol Condensation-Hydrolysis Reaction: Recommending an Improved Organic Synthesis Experiment. University Chemistry, 2024, 39(4): 322-328. doi: 10.3866/PKU.DXHX202309095
9. [9]
  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
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]
  Xinyi MA , Yuhang XIAO , Qian LI , Zihuan YAN , Chengyan LIU , Xiguang GAO , Hongju YIN , Feixiang CHENG . Thienyl metal coordination polymers: Preparation and photocatalytic degradation performance of phenol. Chinese Journal of Inorganic Chemistry, 2026, 42(5): 969-979. doi: 10.11862/CJIC.20250317
12. [12]
  Qi Wang , Yuqing Liu , Jiefei Wang , Yuan-Yuan Ma , Jing Du , Zhan-Gang Han . Catalysts for electrocatalytic dechlorination of chlorinated aromatic hydrocarbons: synthetic strategies, applications, and challenges. Acta Physico-Chimica Sinica, 2025, 41(10): 100120-0. doi: 10.1016/j.actphy.2025.100120
13. [13]
  Bingliang Li , Yuying Han , Dianyang Li , Dandan Liu , Wenbin Shang . One-Step Synthesis of Benorilate Guided by Green Chemistry Principles and in vivo Dynamic Evaluation. University Chemistry, 2024, 39(6): 342-349. doi: 10.3866/PKU.DXHX202311070
14. [14]
  Ranhui Fu , Shixin Zhou , Ran Ji , Feifei Gao , Hui Xu . 季膦盐合成实验的改进与拓展——水相一步法合成乙基三苯基溴化膦及其力致发光锰配合物的制备及表征. University Chemistry, 2026, 41(5): 252-263. doi: 10.12461/PKU.DXHX202510018
15. [15]
  Lifang HE , Wenjie TANG , Yaoze LUO , Mingsheng LIANG , Jianxin TANG , Yuxuan WU , Fuxing ZHANG , Xiaoming 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
16. [16]
  Bolin Sun , Jie Chen , Ling Zhou . 乙烯型卤代烃的亲核取代反应. University Chemistry, 2025, 40(8): 152-157. doi: 10.12461/PKU.DXHX202410032
17. [17]
  Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO₂ by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
18. [18]
  Jiaojiao Yu , Bo Sun , Na Li , Cong Wen , Wei Li . Improvement of Classical Organic Experiment Based on the “Reverse-Step Optimization Method”: Taking Synthesis of Ethyl Acetate as an Example. University Chemistry, 2025, 40(3): 333-341. doi: 10.12461/PKU.DXHX202405177
19. [19]
  Dongheng WANG , Si LI , Shuangquan ZANG . Construction of chiral alkynyl silver chains and modulation of chiral optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 131-140. doi: 10.11862/CJIC.20240379
20. [20]
  Yue Zhao , Yanfei Li , Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(2987)
HTML views(287)

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