通过C(sp3)—H键直接官能团化高效合成1-芳基烯基膦酸酯
收稿日期: 2018-03-13
修回日期: 2018-05-05
网络出版日期: 2018-06-01
基金资助
国家自然科学基金（Nos.21462056，21801261）、贵州省联合基金（No.[2014]7542）和遵义医学院（Nos.20163715，F-627）资助项目.
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).
直接对磷酰基邻位的C（sp3）—H键进行官能团化来合成烯基膦酸酯的研究非常少见.通过苄基膦酸酯与多聚甲醛在温和的碱性条件下，使用四叔丁基碘化铵催化可以在空气中高效简便地合成烯烃膦酸酯，底物适用范围广，可获得中等至优秀的产率.
关键词： 膦酸酯; 烯烃化; C(sp3)—H键官能团化; Horner-Wadsworth-Emmons反应
任林静 , 冉茂刚 , 方学红 , 赵玲 , 姚秋丽 . 通过C(sp3)—H键直接官能团化高效合成1-芳基烯基膦酸酯[J]. 有机化学, 2018 , 38(10) : 2791 -2797 . DOI: 10.6023/cjoc201803016
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.
[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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