Chinese Journal of Organic Chemistry >
Effective Transformation of Alkynylphosphonates into β-Ketophosphonates with a Gold(I) Catalyst
Received date: 2014-04-24
Revised date: 2014-09-03
Online published: 2014-09-09
Supported by
Project supported by the Science and Technology Planning Project of Hunan Province (No. 2014FJ3053), the National Natural Science Foundation of China (No. 21176061), the Natural Science Foundation of Hunan Province (No. 13JJ3132), the Construct Program of the Key Discipline in Hunan Province and Science and Technology Planning Project of Hengyang City (No. 2014FJ3053).
β-Ketophosphonates are an important class of carbonyl compounds which exhibit a wide range of biological activities and outstanding metal-complexing abilities. They are building blocks in organic synthesis, especially as intermediates for the synthesis of α,β-unsaturated carbonyl compounds, chrial β-hydroxy and β-hydroxy phosphonic acids. In this paper, a simple, convenient and environmentally benign method to synthesize the β-ketophosphonates from alkynylphosphonates was developed, which can be easily prepared in one step from commercial terminal alkynes. In the presence of 2.5 mol% XPhosAuSbF6 and 3 equiv. of water in dichloroethane at room temperature, a broad range of alkynylphosphonates were converted into the corresponding β-ketophosphonates in nearly equivalent conversion through gold-catalyzed hydration reaction. The presented methodology will provide new strategies for β-ketophosphonates-type natural product and drug synthesis, which has important academic significance and application value.
Key words： alkynylphosphonates; β-ketophosphonate; gold catalysis; hydration reaction
Liu Kaijian , Liu Hongwei , Wang Wenge , Ou Lijuan , Wang Jingjing , Hu Bonian . Effective Transformation of Alkynylphosphonates into β-Ketophosphonates with a Gold(I) Catalyst[J]. Chinese Journal of Organic Chemistry, 2014 , 34(10) : 2007 -2014 . DOI: 10.6023/cjoc201404046
[1] Beller, M.; Seayad, J.; Tillack, A.; Jiao, H. Angew. Chem., Int. Ed. 2004, 43, 3368.
[2] Hintermann, L.; Labonne, A. Synthesis 2007, 1121.
[3] Kutscheroff, M. Chem. Ber. 1881, 14, 1540.
[4] Suzuki, T.; Tokunaga, M.; Wakatsuki, Y. Org. Lett. 2001, 3, 735.
[5] Tokunaga, M.; Suzuki, T.; Koga, N.; Fukushima, T.; Horiuchi, A.; Wakatsuki, Y. J. Am. Chem. Soc. 2001, 123, 11917.
[6] Baidossi, W.; Lahav, M.; Blum, J. J. Org. Chem. 1997, 62, 669.
[7] Trentin, F.; Chapman, A. M.; Scarso, A.; Sgarbossa, P.; Michelin, R. A.; Strukul, G. D.; Wass, F. Adv. Synth. Catal. 2012, 354, 1095.
[8] Wu, X.-F.; Bezier, D.; Darcel, C. Adv. Synth. Catal. 2009, 351, 367.
[9] Cabrero-Antonino, J. R.; Leyva-Pérez, A.; Corma, A. Chem.-Eur. J. 2012, 18, 11107.
[10] Park, J.; Yeon, J.; Lee, P. H.; Lee, K. Tetrahedron Lett. 2013, 54, 4414.
[11] Das, R.; Chakraborty, D. Appl. Organomet. Chem. 2012, 26, 722.
[12] Thuong, M. B. T.; Mann, A.; Wagner, A. Chem. Commun. 2012, 48, 434.
[13] Chen, Z.-W.; Ye, D.-N.; Qian, Y.-P.; Ye, M.; Liu, L.-X. Tetrahedron 2013, 69, 6116.
[14] Tachinami, T.; Nishimura, T.; Ushimaru, R.; Noyori, R.; Naka, H. J. Am. Chem. Soc. 2012, 135, 50.
[15] Wong, W.-L.; Ho, K.-P.; Lee, L. Y. S.; Lam, K.-M.; Zhou, Z.-Y.; Chan, T. H.; Wong, K.-Y. ACS Catal. 2011, 1, 116.
[16] Ackermann, L.; Kaspar, L. T. J. Org. Chem. 2007, 72, 6149.
[17] Wang, S.; Zhang, G.; Zhang, L. Synlett 2010, 692.
[18] Huang, H.; Zhou, Y.; Liu, H. Beilstein J. Org. Chem. 2011, 7, 897.
[19] Xiao, J.; Li, X. Angew. Chem., Int. Ed. 2011, 50, 7226.
[20] Lu, B.-L.; Dai, L.; Shi, M. Chem. Soc. Rev. 2012, 41, 3318 (in Chinese).
[21] Zhang, Y.; Luo, S.; Zhu, C. J. Chin. J. Org. Chem. 2012, 32, 2073 (in Chinese).
(张艳, 罗莎, 朱成建, 有机化学, 2012, 32, 2073.)
[22] Fukuda, Y.; Utimoto, K. J. Org. Chem. 1991, 56, 3729.
[23] Mizushima, E.; Sato, K.; Hayashi, T.; Tanaka, M. Angew. Chem., Int. Ed. 2002, 41, 4563.
[24] Casado, R.; Contel, M.; Laguna, M.; Romero, P.; Sanz, S. J. Am. Chem. Soc. 2003, 125, 11925.
[25] Roembke, P.; Schmidbaur, H.; Cronje, S.; Raubenheimer, H. J. Mol. Catal. A: Chem. 2004, 212, 35.
[26] Marion, N.; Ramón, R. n. S.; Nolan, S. P. J. Am. Chem. Soc. 2009, 131, 448.
[27] Ghosh, N.; Nayak, S.; Sahoo, A. K. J. Org. Chem. 2010, 76, 500.
[28] Czégéni, C. E.; Papp, G.; Kathó, Á.; Joó, F. J. Mol. Catal. A: Chem. 2011, 340, 1.
[29] Nun, P.; Ramón, R. S.; Gaillard, S.; Nolan, S. P. J. Organomet. Chem. 2011, 696, 7.
[30] Xu, X.; Kim, S. H.; Zhang, X.; Das, A. K.; Hirao, H.; Hong, S. H. Organometallics 2012, 32, 164.
[31] Tubaro, C.; Baron, M.; Biffis, A.; Basato, M. Beilstein J. Org. Chem. 2013, 9, 246.
[32] Kondoh, A.; Yorimitsu, H.; Oshima, K. Chem. Asian J. 2010, 5, 398.
[33] Zhou, Y.; Wang, G.; Saga, Y.; Shen, R.; Goto, M.; Zhao, Y.; Han, L.-B. J. Org. Chem. 2010, 75, 7924.
[34] Li, Y.; Das, S.; Zhou, S.; Junge, K.; Beller, M. J. Am. Chem. Soc. 2012, 134, 9727.
[35] Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863.
[36] Pronin, S. V.; Martinez, A.; Kuznedelov, K.; Severinov, K.; Shuman, H. A.; Kozmin, S. A. J. Am. Chem. Soc. 2011, 133, 12172.
[37] Ryglowski, A.; Kafarski, P. Tetrahedron 1996, 52, 10685.
[38] Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2931.
[39] Chávez, M. Á.; Vargas, S.; Suárez, A.; Álvarez, E.; Pizzano, A. Adv. Synth. Catal. 2011, 353, 2775.
[40] Li, X.; Hu, G.; Luo, P.; Tang, G.; Gao, Y.; Xu, P.; Zhao, Y. Adv. Synth. Catal. 2012, 354, 2427.
[41] Wei, W.; Ji, J.-X. Angew. Chem., Int. Ed. 2011, 50, 9097.
[42] Maloney, K. M.; Chung, J. Y. L. J. Org. Chem. 2009, 74, 7574.
[43] Koprowski, M.; Szymańska, D.; Bodzioch, A.; Marciniak, B.; Ró?ycka-Soko?owska, E.; Ba?czewski, P. Tetrahedron 2009, 65, 4017.
[44] Milburn, R. R.; McRae, K.; Chan, J.; Tedrow, J.; Larsen, R.; Faul, M. Tetrahedron Lett. 2009, 50, 870.
[45] Gao, Y.; Wang, G.; Chen, L.; Xu, P.; Zhao, Y.; Zhou, Y.; Han, L.-B. J. Am. Chem. Soc. 2009, 131, 7956.
[46] Toy, A. D. F.; Walsh, E. N. In Phosphorus Chemistry in Everyday Living, American Chemical Society, Washington D. C., 1987.
[47] Essid, I.; Touil, S. ARKIVOC 2013, 4, 98.
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