Browse > Article
http://dx.doi.org/10.5012/bkcs.2013.34.9.2645

Synthesis of 2-Substituted Benzofurans from o-Iodophenols and Terminal Alkynes with a Recyclable Palladium Catalyst Supported on Nano-sized Carbon Balls under Copper- and Ligand-Free Conditions  

Yum, Eul Kgun (Department of Chemistry, Chungnam National University)
Yang, Ok-Kyung (Department of Chemistry, Chungnam National University)
Kim, Ji-Eun (Department of Chemistry, Chungnam National University)
Park, Hee Jung (Korea Basic Science Institute)
Publication Information
Abstract
We have developed a one-step synthesis of benzofurans from o-iodophenol and various terminal alkynes, by using Pd catalyst supported on nano-sized carbon balls (NCB) under copper- and ligand free conditions. This recyclable catalyst could be reused more than 5 times in the same heteroannulation reaction. The results have demonstrated that diverse 2-substituted benzofurans with tolerant functional groups can be prepared simply and conveniently under these conditions.
Keywords
Benzofuran; Nano-sized carbon balls; Terminal alkynes; Recyclable; Palladium catalyst;
Citations & Related Records
Times Cited By KSCI : 2  (Citation Analysis)
연도 인용수 순위
1 Baghbanzadeh, M.; Pilger, C.; Kappe, C. O. J. Org. Chem. 2011, 76, 8138-8142.   DOI   ScienceOn
2 Alam, M. J.; Rashid, M. A.; Chowdhury, R. Bioorg. Med. Chem. 2005, 13, 4796-4805.   DOI   ScienceOn
3 Lee, J. K.; Han, S. Y.; Park, S.-K.; Park, Y.-K.; Lee, C. W. Korean J. Chem. Eng. 2005, 22, 42-45.   DOI   ScienceOn
4 Yum, E. K.; Son, J. W.; Kim, S. K.; Kim, S. N.; Kim, K. M.; Lee, C. W. Bull. Korean Chem. Soc. 2010, 31, 2097-2099.   DOI   ScienceOn
5 Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V. Comprehensive Heterocyclic Chemistry; Pergamon Press: 1996, 4, 395-436.
6 Ohtaka, A.; Teratani, T.; Fujii, R.; Ikeshita, K.; Kawashima, T.; Tatsumi, K.; Shimomura, O.; Nomura, R. J. Org. Chem. 2011, 76, 4052-4060.   DOI   ScienceOn
7 Priyadarshini, S.; Amal-J, P. J.; Srinivas, P.; Maheswaran, H.; Lakshmi-K, M.; Bhargava, S. Tetrahedron Lett. 2011, 52, 1615-1618.   DOI   ScienceOn
8 Saejueng, P.; Bates, C. G.; Venkataraman, D. Synthesis 2005, 10, 1706-1712.
9 Wang, R.-P.; Mo, S.; Lu, Y.-Z.; Shen, Z.-M. Adv. Synth. Catal. 2011, 353, 713-718.   DOI   ScienceOn
10 Gil-M., J.; Najera, C. Eur. J. Org. Chem. 2005, 19, 4073-4081.
11 Elangovan, A.; Yang, S.-W.; Lin, J.-H.; Kao, K.- M.; Ho, T.-I. Org. Biomol. Chem. 2004, 2, 1597-1602.   DOI   ScienceOn
12 Fujii, S.; Matsuzawa, S.; Hamasaki, H.; Nakamura, Y.; Bouleghlimat, A.; Buurma, N. J. Langmuir 2012, 28, 2436-2447.   DOI   ScienceOn
13 Cano, M.; Benito, A.; Maser, W. K.; Urriolabeitia, E. P. Carbon 2011, 49, 652-658.   DOI   ScienceOn
14 Kabalka, G. W.; Wang, L.; Pagni, R. M. Tetrahedron 2001, 57, 8017-8028.   DOI   ScienceOn
15 Kundu, N. G.; Pal, M.; Mahanty, J. S.; De, M. J. Chem. Soc. Perkin. Trans. 1 1997, 19, 2815-2820.
16 Hercouet, A.; Le Corre, M. Tetrahederon 1981, 37, 2867-2873.   DOI   ScienceOn
17 Cano, R.; Yus, M.; Ramon, D. J. Tetrahedron 2012, 68, 1393-1400.   DOI   ScienceOn
18 Pal, M.; Subramanian, V.; Yeleswarapu, K. R. Tetrahedron Lett. 2003, 44, 8221-8225.   DOI   ScienceOn
19 Tye, H.; Whittaker, M.; Ramdeehul, S. Com. Chem. High. T. Scr. 2006, 9, 703-710.
20 Panda, A. G.; Patil, Y. P.; Tambade, P. J.; Bhanage, B. M. Ind. Eng. Chem. Res. 2010, 49, 8360-8364.   DOI   ScienceOn
21 Wan, Y.; Wang, H.; Zhao, Q.; Klingstedt, M.; Terasaki, O.; Zhao, D. J. Am. Chem. Soc. 2009, 131, 4541-4550.   DOI   ScienceOn
22 Karimi, B.; Fadavi-A. P. Chem. Commun. 2009, 25, 3750-3752.
23 Kleist, W.; Lee, J.-K.; Koehler, K. Eur. J. Inorg. Chem. 2009, 2, 261-266.
24 Wang, P.; Wang, Z.; Li, J.; Bai, Y. Micropor. Mesopor. Mater. 2008, 116, 400-405.   DOI   ScienceOn
25 Karimi, B.; Enders, D. Org. Lett. 2006, 8, 1237-1240.   DOI   ScienceOn
26 Zhang, X.; Li, P.; Ji, Y.; Zhang, L.; Wang, L. Synthesis 2011, 18, 2975-2983.
27 Liu, J.; Peng, X.; Sun, W.; Zhao, Y.; Xia, C. Org. Lett. 2008, 10, 3933-3936.   DOI   ScienceOn
28 Xu, L.; Shen, X.-X.; Xiao, Q.; Zhong, Y.-J.; Ye, S.-F.; Ye, X.-R.; Zhu, W.-D. Wuli Huaxue Xuebao 2011, 27, 1956-1960.
29 Garcia-S., E. J.; Tristany, M.; Garcia, A. B.; Colliere, V.; Philippot, K. Micropor. Mesopor. Mater. 2012, 153, 155-162.   DOI   ScienceOn
30 Khedkar, M. V.; Khan, S. R.; Sawant, D. N.; Bagal, D. B.; Bhanage, B. M. Adv. Synth. Catal. 2011, 353, 3415-3422.   DOI   ScienceOn
31 Calvino-C, V.; Lopez-P, A. J.; Duran-V, C. J.; Martin-A, R. M. Catal. Rev. Sci. Engin. 2010, 52, 325-380.   DOI   ScienceOn