Chinese Journal of Organic Chemistry >
An Efficient Synthesis of 1-Arylvinylphosphonates via Direct Functionalization of C (sp3)—H Bond
Received date: 2018-03-13
Revised date: 2018-05-05
Online published: 2018-06-01
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21462056, 21801261), the Science and Technology Foundation of Guizhou Province (No.[2014]7542) and the Zunyi Medical University (Nos. 20163715, F-627).
The direct functionalization of the C (sp3)—H bond adjacent to the phosphonate group for the preparation of vinyl phosphonates was rarely developed. Herein, a simple and efficient tetrabutylammonium iodide catalyzed protocol for the preparation of vinyl phosphonates from benzylic phosphonates and paraformaldehyde is achieved under mild conditions in air. Moderate to high yields can be obtained for a broad scope of substrates.
Ren Linjing , Ran Maogang , Fang Xuehong , Zhao Ling , Yao Qiuli . An Efficient Synthesis of 1-Arylvinylphosphonates via Direct Functionalization of C (sp3)—H Bond[J]. Chinese Journal of Organic Chemistry, 2018 , 38(10) : 2791 -2797 . DOI: 10.6023/cjoc201803016
[1] Bekheit, M. S.; Kamel, A. A. Curr. Org. Chem. 2017, 21, 923.
[2] Luo, K.; Yang, W.-C.; Wu, L. Asian J. Org. Chem. 2017, 6, 350.
[3] Novakov, I. A.; Rakhimov, A. I. Russ. J. Gen. Chem. 2016, 86, 508.
[4] Virieux, D.; Sevrain, N.; Ayad, T.; Pirat, J.-L. Adv. Heterocycl. Chem. 2015, 116, 37.
[5] Demkowicz, S.; Rachon, J.; Dasko, M.; Kozak, W. RSC Adv. 2016, 6, 7101.
[6] Grzywa, R.; Sienczyk, M. Curr. Pharm. Des. 2013, 19, 1154.
[7] Ruiz, M.; Fernández, M. C.; Díaz, A.; Quintela, J. M.; Ojea, V. J. Org. Chem. 2003, 68, 7634.
[8] Bou Orm, N.; Dkhissi, Y.; Daniele, S.; Djakovitch, L. Tetrahedron 2013, 69, 115.
[9] Soller, B. S.; Salzinger, S.; Rieger, B. Chem. Rev. (Washington, DC, U. S.) 2016, 116, 1993.
[10] Cheruku, P.; Paptchikhine, A.; Church, T. L.; Andersson, P. G. J. Am. Chem. Soc. 2009, 131, 8285.
[11] Okauchi, T.; Nakamura, S.; Tsubaki, K.; Asakawa, M.; Kitamura, M. Carbohydr. Res. 2017, 448, 24.
[12] Benmeddah, A.; Villemin, D.; Mostefa-Kara, B.; Bar, N.; Legay, R. Can. J. Chem. 2017, 95, 871.
[13] Jia, Z.-J.; Jiang, H.; Li, J.-L.; Gschwend, B.; Li, Q.-Z.; Yin, X.; Grouleff, J.; Chen, Y.-C.; Jorgensen, K. A. J. Am. Chem. Soc. 2011, 133, 5053.
[14] Colonna, S.; Gaggero, N.; Carrea, G.; Ottolina, G.; Pasta, P.; Zambianchi, F. Tetrahedron Lett. 2002, 43, 1797.
[15] Shi, B.; Fang, Y.; Zhang, L.; Jin, X.; Wu, Y.; Fang, M.; Yang, Y.; Chen, C. Chin. J. Org. Chem. 2016, 36, 673(in Chinese). (施波超, 方烨汶, 张莉, 金小平, 武永辉, 方媚, 杨宇飞, 陈冲, 有机化学, 2016, 36, 673.)
[16] Dembitsky, V. M.; Quntar, A. A. A.; Haj-Yehia, A.; Srebnik, M. Mini-Rev. Org. Chem. 2005, 2, 91.
[17] Dong, K.; Wang, Z.; Ding, K. J. Am. Chem. Soc. 2012, 134, 12474.
[18] Chen, H.-X.; Huang, L.-J.; Liu, J.-B.; Weng, J.; Lu, G. Phosphorus, Sulfur Silicon Relat. Elem. 2014, 189, 1858.
[19] Fang, Y.; Zhang, L.; Li, J.; Jin, X.; Yuan, M.; Li, R.; Wu, R.; Fang, J. Org. Lett. 2015, 17, 798.
[20] Zhou, Y.; Ye, F.; Wang, X.; Xu, S.; Zhang, Y.; Wang, J. J. Org. Chem. 2015, 80, 6109.
[21] Xue, J.-F.; Zhou, S.-F.; Liu, Y.-Y.; Pan, X.; Zou, J.-P.; Asekun, O. T. Org. Biomol. Chem 2015, 13, 4896.
[22] Felpin, F.-X.; Miqueu, K.; Sotiropoulos, J.-M.; Fouquet, E.; Ibarguren, O.; Laudien, J. Chem.-Eur. J. 2010, 16, 5191.
[23] Zhang, N.; Casida, J. E. Bioorg. Med. Chem. 2002, 10, 1281.
[24] Eichler, M. C.; Grayson, D. H.; Huddleston, J.; O'Neill, J. P. Tetrahedron 2014, 70, 7241.
[25] Baird, L. J.; Colomban, C.; Turner, C.; Teesdale-Spittle, P. H.; Harvey, J. E. Org. Biomol. Chem 2011, 9, 4432
[26] Mohamed-Hachi, A.; About-Jaudet, E.; Combret, J. C.; Collignon, N. Synthesis 1997, 653.
[27] Degenhardt, C. R.; Burdsall, D. C. J. Org. Chem. 1986, 51, 3488.
[28] Rathke, M. W.; Nowak, M. J. Org. Chem. 1985, 50, 2624.
[29] Te Grotenhuis, C.; van den Heuvel, N.; van der Vlugt, J. I.; de Bruin, B. Angew. Chem., Int. Ed. 2018, 57, 140.
[30] Tateishi, H.; Tsuji, A. B.; Kato, K.; Sudo, H.; Sugyo, A.; Hanakawa, T.; Zhang, M.-R.; Saga, T.; Arano, Y.; Higashi, T. Bioorg. Med. Chem. Lett. 2017, 27, 4893.
[31] Luo, X.; Fang, Y.; Fan, Y.-H.; Zhang, L. Chem. Reag. 2009, 31, 974(in Chinese). (罗炫, 方瑜, 范勇恒, 张林, 化学试剂, 2009, 31, 974.)
[32] Wang, D.-Y.; Hu, X.-P.; Deng, J.; Yu, S.-B.; Duan, Z.-C.; Zheng, Z. J. Org. Chem. 2009, 74, 4408.
[33] Karimov, K. R.; Shakhidoyatov, K. M.; Alovitdinov, A. B.; Kuchkarov, A. B. Zh. Obshch. Khim. 1984, 54, 2393.
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