γ-Aluminum Oxide-Mediated Iodination of Terminal Alkynes
- Corresponding author: Yao Ming, yaomingcep@jcut.edu.cn Xiong Hangxing, 731990153@qq.com
Citation:
Yao Ming, Zhang Jingjing, Yang Sen, Xiong Hangxing. γ-Aluminum Oxide-Mediated Iodination of Terminal Alkynes[J]. Chinese Journal of Organic Chemistry,
;2020, 40(7): 2153-2158.
doi:
10.6023/cjoc202002014
Jeschke, P. Pest Manage. Sci. 2010, 66, 10.
doi: 10.1002/ps.1829
Hernandes, M. Z.; Cavalcanti, S. M. T.; Moreira, D. R. M.; de Azevedo, W. F.; Leite, A. C. L. Curr. Drug Targets 2010, 11, 303.
doi: 10.2174/138945010790711996
Tang, M. L.; Bao, Z. Chem. Mater. 2011, 23, 446.
doi: 10.1021/cm102182x
Wilcken, R.; Zimmermann, M. O.; Lange, A.; Joerger, A. C.; Boeckler, F. M. J. Med. Chem. 2013, 56, 1363.
Petrone, D. A.; Ye, J.; Lautens, M. Chem. Rev. 2016, 116, 8003.
doi: 10.1021/acs.chemrev.6b00089
Agarwal, V.; Miles, Z. D.; Winter, J. M.; Eustaquio, A. S.; El Gamal, A. A.; Moore, B. S. Chem. Rev. 2017, 117, 5619.
doi: 10.1021/acs.chemrev.6b00571
Lin, R.; Amrute, A. P.; Perez-Ramirez, J. Chem. Rev. 2017, 117, 4182.
doi: 10.1021/acs.chemrev.6b00551
Berger, G.; Robeyns, K.; Soubhye, J.; Wintjens, R.; Meyer, F. CrystEngComm 2016, 18, 683.
doi: 10.1039/C5CE02230D
Yauchi, Y.; Ide, M.; Shiogai, R.; Chikugo, T.; Iwasawa, T. Eur. J. Org. Chem. 2015, 938.
Morisawa, Y.; Konishi, K.; Kataoka, M. US 4487781, 1984.
Sriramoju, V.; Jillella, R.; Kurva, S.; Madabhushi, S. Chem. Lett. 2017, 46, 560.
doi: 10.1246/cl.161171
Liu, Y.; Huang, D.; Huang, J.; Maruoka, K. J. Org. Chem. 2017, 82, 11865.
Rather, S. A.; Kumar, A.; Ahmed, Q. N. Chem. Commun. 2019, 55, 4511.
doi: 10.1039/C9CC00346K
Smith, K. Solids Supports and Catalysts in Organic Synthesis, Ellis Horwood, Chichester, UK, 1992.
Busca, G. Heterogeneous Catalytic Materials: Solid State Chemistry, Surface Chemistry and Catalytic Behavior, Elsevier, Amsterdam, 2014.
Pines, H.; Haag, W. O. J. Am. Chem. Soc. 1960, 82, 2471.
doi: 10.1021/ja01495a021
Corado, A.; Kiss, A.; Knozinger, H.; Muller, H. D. J. Catal. 1975, 37, 68.
doi: 10.1016/0021-9517(75)90134-7
Quici, S.; Regen, S. L. J. Org. Chem. 1979, 44, 3436.
doi: 10.1021/jo01333a045
Pannell, K. H.; Mayr, A. J. J. Chem. Soc., Perkin Trans. 1 1982, 2153.
Tundo, P.; Venturello, P.; Angeletti, E. J. Chem. Soc., Perkin Trans. 2 1983, 485.
Boothe, R.; Dial, C.; Conaway, R.; Pagni, R. N.; Kabalka, G. W. Tetrahedron Lett. 1986, 27, 2207.
Pagni, M. R.; Kaballaka, G. W.; Boothe, R.; Gaetano, K.; Stewart, L. J. Stud. Org. Chem. (Amsterdam) 1987, 31, 399.
Kodomari, M.; Takahshi, S.; Yoshitomi, S. Chem. Lett. 1987, 1901.
Kodomari, M.; Takahshi, S.; Yoshitomi, S. J. Org. Chem. 1988, 53, 2093.
doi: 10.1021/jo00244a046
Kodomari, M.; Takahshi, S.; Yoshitomi, S. Bull. Chem. Soc. Jpn. 1988, 61, 4149.
doi: 10.1246/bcsj.61.4149
Binns, S.; Green, J.; Tan, L. C.; Pangi, R. M.; Kabalka, G. W. J. Org. Chem. 1992, 57, 7475.
Ranu, B. C.; Sarkar, D. C.; Dispak, C.; Chakraborty, R. Synth. Commun. 1992, 22, 1095.
doi: 10.1080/00397919208021092
Singh, P. K.; Khanna, R. N. Synth. Commun. 1993, 23, 2083.
doi: 10.1080/00397919308018601
Stavber, S.; Jereb, M.; Zupan, M. Synthesis 2008, 1487.
Larson, S.; Luidhardt, T.; Kabalka, G. W.; Pagni, R. M. Tetrahedron Lett. 1988, 29, 35.
doi: 10.1016/0040-4039(88)80009-1
Hondrogiannis, G.; Lee, L. C.; Abalka, G. W.; Pagni, R. M. Tetrahedron Lett. 1989, 30, 2069.
doi: 10.1016/S0040-4039(01)93713-X
Yao, M.; Zhang, J.; Yang, S.; Xiong, H.; Li, L.; Liu, E.; Shi, H. RSC Adv. 2020, 10, 3946.
doi: 10.1039/D0RA00251H
Chen, S.; Zhang, X.; Zhao, H.; Guo, X.; Hu, X. Chin. J. Org. Chem. 2018, 38, 1172 (in Chinese).
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