Progress in the Synthesis of Arylphosphonates via Ar-P Bond Construction

doi:10.6023/cjoc202002006

Abstract

Arylphosphonates and their derivatives are an important class of molecules because of their broad application in medicinal chemistry, material chemistry and organic catalysis. On basis of various aryl sources for the Ar-P bond construction, the recent advances in the development of the synthesis of arylphosphonates catalyzed by transition metals and photoinduced are surveyed.

Key words: arylphosphonate, Ar-P bond construction, transition-metal catalysis, light induced, electrochemical, aryl source

Cite this article

Sun Kai, Liu Haidong, Xie Qi, Luo Haiqing. Progress in the Synthesis of Arylphosphonates via Ar-P Bond Construction[J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2275-2289.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Baumgartner, T.; Réau, R. Chem. Rev. 2006, 106, 4681.
[2] White, A. K.; Metcalf, W. W. Annu. Rev. Microbiol. 2007, 61, 379.
[3] Clercq, E. D. Med. Res. Rev. 2009, 30, 667.
[4] Iaroshenko, V. In Organophosphorus Chemistry:From Molecules to Applications, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2019, p. 59.
[5] Schwan, A. L. Chem. Soc. Rev. 2004, 33, 218.
[6] Van der Jeught, S.; Stevens, C. V. Chem. Rev. 2009, 109, 2672.
[7] Henyecz, R.; Keglevich, G. Curr. Org. Synth. 2019, 16, 523.
[8] Cai, B.-G.; Xuan, J.; Xiao, W.-J. Sci. Bull. 2019, 64, 337.
[9] Chen, T.; Zhang, J.-S.; Han, L.-B. Dalton Trans. 2016, 45, 1843.
[10] (a) Budnikova, Y. H.; Gryaznova, T. V.; Grinenko, V. V.; Dudkina, Y. B.; Khrizanforov, M. N. Pure Appl. Chem. 2017, 89, 311.
(b) Budnikova, Y. H.; Sinyashin, O. G. Russ. Chem. Rev. 2015, 84, 917.
[11] (a) Jiménez, M. V.; Pérez-Torrente, J. J.; Bartolomé, M. I.; Oro, L. A. Synthesis 2009, 1916.
(b) Yang, Y.; Qiu, X.; Zhao, Y.; Mu, Y.; Shi, Z. J. Am. Chem. Soc. 2016, 138, 495.
[12] Hirao, T.; Masunaga, T.; Ohshiro, Y.; Agawa, T. Synthesis 1981, 56.
[13] Hirao, T.; Masunaga, T.; Yamada, N.; Ohshiro, Y.; Agawa, T. Bull. Chem. Soc. Jpn. 1982, 55, 909.
[14] Kalek, M.; Jezowska, M.; Stawinski, J. Adv. Synth. Catal. 2009, 351, 3207.
[15] Kohler, M. C.; Sokol, J. G.; Stockland Jr, R. A. Tetrahedron Lett. 2009, 50, 457.
[16] Xu, J.; Zhang, P.; Gao, Y.; Chen, Y.; Tang, G.; Zhao, Y. J. Org. Chem. 2013, 78, 8176.
[17] Huang, C.; Tang, X.; Fu, H. Jiang, Y.; Zhao, Y. J. Org. Chem. 2006, 71, 5020.
[18] Ballester, J.; Gatignol, J.; Schmidt, G.; Alayrac, C.; Gaumont, A.-C.; Taillefer, M. ChemCatChem 2014, 6, 1549.
[19] Zhao, Y. L.; Wu, G. J.; Li, Y.; Gao, L. X.; Han, F. S. Chem.-Eur. J. 2012, 18, 9622.
[20] Kinbara, A.; Ito, M.; Abe, T.; Yamagishi, T. Tetrahedron 2015, 71, 7614.
[21] Kalek, M.; Ziadi, A.; Stawinski, J. Org. Lett. 2008, 10, 4637.
[22] Jablonkai, E.; Keglevich, G. Tetrahedron Lett. 2014, 44, 4185.
[23] Shaikh, R. S.; Düsel, S. J. S.; König, B. ACS Catal. 2016, 6, 8410.
[24] Ghosh, I.; Shaikh, R. S.; König, B. Angew. Chem., Int. Ed. 2017, 129, 8664.
[25] Lecroq, W.; Bazille, P.; Morlet-Savary, F.; Breugst, M.; Lalevée, J.; Gaumont, A.-C.; Lakhdar, S. Org. Lett. 2018, 20, 4164.
[26] Zeng, H.; Dou, Q.; Li, C.-J. Org. Lett. 2019, 21, 1301.
[27] Sengmany, S.; Ollivier, A.; Le Gall, E.; Léonel, E. Org. Biomol. Chem. 2018, 16, 4495.
[28] Wang, S.; Yang, C.; Sun, S.; Wang, J. Chem. Commun. 2019, 55, 14035.
[29] Bai, Y.; Liu, N.; Wang, S.; Wang, S.; Ning, S.; Shi, L.; Cui, L.; Zhang, Z.; Xiang, J. Org. Lett. 2019, 21, 6835.
[30] Andaloussi, M.; Lindh, J.; Savmarker, J.; Sjoberg, P. J. R.; Larhed, M. Chem.-Eur. J. 2009, 15, 13069.
[31] Zhuang, R.; Xu, J.; Cai, Z.; Tang, G.; Fang, M.; Zhao, Y. Org. Lett. 2011, 13, 2110.
[32] Hu, G.; Chen, W.; Fu, T.; Peng, Z.; Qiao, H.; Gao, Y.; Zhao, Y. Org. Lett. 2013, 15, 5362.
[33] Hicks, I.; McTague, J.; Hapatsha, T.; Teriak, R.; Kaur, P. Molecules 2020, 25, 290.
[34] Chen, T.-H.; Reddy, D. M.; Lee, C.-F. RSC Adv. 2017, 7, 30214.
[35] Berrino, R.; Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Stabile, P. Org. Biomol. Chem. 2010, 8, 4518.
[36] He, Y.; Wu, H.; Toste, F. D. Chem. Sci. 2015, 46, 1194.
[37] Wang, S.; Qiu, D.; Mo, F.; Zhang, Y.; Wang, J. J. Org. Chem. 2016, 81, 11603.
[38] Xu, W.; Hu, G.; Xu, P.; Gao, Y.; Yin, Y.; Zhao, Y. Adv. Synth. Catal. 2014, 14, 2948.
[39] Chen, S.-Y.; Zeng, R.-S.; Zou, J.-P.; Asekun, O. T. J. Org. Chem. 2014, 79, 1449.
[40] Li, R.; Chen, X.; Wei, S.; Sun, K.; Fan, L.-L.; Liu, Y.; Qu, L.; Zhao, Y.; Yu, B. Adv. Synth. Catal. 2018, 360, 4807.
[41] Qiu, D.; Lian, C.; Mao, J.; Ding, Y.; Liu, Z.; Wei, L.; Fagnoni, M.; Protti, S. Adv. Synth. Catal. 2019, 361, 5239.
[42] Jian, Y.; Chen, M.; Huang, B.; Jia, W.; Yang, C.; Xia, W. Org. Lett. 2018, 20, 5370.
[43] Yang, G.; Shen, C.; Zhang, L.; Zhang, W. Tetrahedron Lett. 2011, 52, 5032.
[44] Yang, J.; Chen, T.; Han, L.-B. J. Am. Chem. Soc. 2015, 137, 1782.
[45] Yang, J.; Xiao, J.; Chen, T.; Han, L.-B. J. Org. Chem. 2016, 81, 3911.
[46] Liao, L.-L.; Gui, Y.-Y.; Zhang, X.-B.; Shen, G.; Liu, H.-D.; Zhou, W.-J.; Li, J.; Yu, D.-G. Org. Lett. 2017, 19, 3735.
[47] Miao, T.; Wang, L. Adv. Synth. Catal. 2014, 356, 967.
[48] Li, J.; Bi, X.; Wang, H.; Xiao, J. RSC Adv. 2014, 4, 19214.
[49] Yang, J.; Xiao, J.; Chen, T.; Yin, S.-F.; Han, L.-B. Chem. Commun. 2016, 52, 12233.
[50] Feng, C. G.; Ye, M.; Xiao, K.-J.; Li, S.; Yu, J.-Q. J. Am. Chem. Soc. 2013, 135, 9322.
[51] Li, C.; Yano, T.; Ishida N.; Murakami, M. Angew. Chem., Int. Ed. 2013, 52, 9801.
[52] Min, M.; Kang, D.; Jung, S.; Hong, S. Adv. Synth. Catal. 2016, 358, 1296.
[53] Hong, G.; Mao, D.; Wu, S.; Wang, L. J. Org. Chem. 2014, 79, 10629.
[54] Wang, S.; Guo, R.; Wang, G.; Chen, S.-Y.; Yu, X.-Q. Chem. Commun. 2014, 50, 12718.
[55] Hore, S.; Srivastava, A.; Singh, R. P. J. Org. Chem. 2019, 84, 6868.
[56] Effenberger, F.; Kottmann, H. Tetrahedron 1985, 41, 4171.
[57] Mao, X.; Ma, X.; Zhang, S.; Hu, H.; Zhu, C.; Cheng, Y. Eur. J. Org. Chem. 2013, 20, 4245.
[58] Kagayama, T.; Nakano, A.; Sakaguchi, S.; Ishii, Y. Org. Lett. 2006, 8, 407.
[59] Berger, O.; Montchamp, J.-L. J. Org. Chem. 2019, 84, 9239.
[60] Niu, L.; Liu, J.; Yi, H. Wang, S.; Liang, X.-A.; Singh, A. K.; Chiang, C.-W.; Lei, A. ACS Catal. 2017, 7, 7412.
[61] Yuan, Y.; Qiao, J.; Cao, Y.; Tang, J.; Wang, M.; Ke, G.; Lu, Y.; Liu, X.; Lei, A. Chem. Commun. 2019, 55, 4230.
[62] Liu, C.; Szostak, M. Angew. Chem., Int. Ed. 2017, 56, 12718.
[63] Isshiki, R.; Muto, K.; Yamaguchi, J. Org. Lett. 2018, 20, 1150.
[64] Dong, J.; Liu, L.; Ji, X.; Shang, Q.; Liu, L.; Su, L.; Chen, B.; Kan, R.; Zhou, Y.; Yin, S.-F.; Han, L.-B. Org. Lett. 2019, 21, 3198.
[65] Li, J.; Bi, X.; Wang, H.; Xiao, J. Asian J. Org. Chem. 2014, 3, 1113.
[66] Liu, C.; Ji, C.-L.; Zhou, T.; Hong, X.; Szostak, M. Org. Lett. 2019, 21, 9256.
[67] Dhokale, R. A.; Mhaske, S. B. Org. Lett. 2013, 15, 2218.
[68] Chen, Q.; Yan, X.; Du, Z.; Zhang, K.; Wen, C. J. Org. Chem. 2016, 81, 276.
[69] Yang, G.; Shen, C.; Quan, M.; Zhang, W. Tetrahedron 2016, 72, 333.
[70] Wang, T.; Sang, S.; Liu, L.; Qiao, H.; Gao, Y.; Zhao, Y. J. Org. Chem. 2014, 79, 608.
[71] Luo, H.; Liu, H.; Chen, X.; Wang, K.; Luo, X.; Wang, K. Chem. Commun. 2017, 53, 956.
[72] Matsumura, M.; Dong, Y.; Kakusawa, N.; Yasuike, S. Chem. Pharm. Bull. 2015, 63, 130.
[73] Yu, Y.; Yi, S.; Zhu, C.; Hu, W.; Gao, B.; Chen, Y.; Wu, W.; Jiang, H. Org. Lett. 2016, 18, 400.

通过Ar—P键构筑合成芳基膦酸酯类化合物的研究进展