Atherton-Todd反应的研究进展
收稿日期: 2022-10-26
修回日期: 2022-12-05
网络出版日期: 2022-12-21
基金资助
国家自然科学基金(22222109); 国家自然科学基金(21971165); 国家自然科学基金(21921002); 国家重点研发计划(2018YFA0903500); 北京国家分子科学中心项目(BNLMS202101); 中央高校基本科研专项资金和四川大学基本科研专项资金(2020SCUNL108)
Recent Advances of the Atherton-Todd Reaction
Received date: 2022-10-26
Revised date: 2022-12-05
Online published: 2022-12-21
Supported by
National Natural Science Foundation of China(22222109); National Natural Science Foundation of China(21971165); National Natural Science Foundation of China(21921002); National Key R&D Program of China(2018YFA0903500); Beijing National Laboratory for Molecular Sciences(BNLMS202101); Fundamental Research Funds for the Central Universities and the Fundamental Research Funds from Sichuan University(2020SCUNL108)
磷酰胺或磷酸酯类化合物及其衍生物是一类非常重要的含磷有机分子, 在药物化学、材料化学以及有机催化等研究领域均有着广泛应用. Atherton-Todd反应是制备这类化合物最有效的方法之一, 该反应是指氧磷氢化合物[P(O)- H]在碱的作用下与四氯化碳原位生成磷酰氯[P(O)-Cl]中间体, 随后该中间体与醇或胺类化合物反应形成相应的磷酸酯或磷酰胺类化合物及其衍生物. 近年来, Atherton-Todd反应由于其操作容易、原子经济性高、底物普适性广以及易于将含磷原子引入到活性化合物结构片段中等优点, 受到了合成化学家的广泛关注. 总结近几十年来Atherton-Todd反应的研究进展及其在有机合成中的应用, 并对目前该领域可能存在的研究挑战提出展望, 希望能为Atherton-Todd反应的未来发展方向提供一些借鉴和思考.
关键词： 有机磷化合物; Atherton-Todd反应; 活性中间体; 不对称催化
方思强 , 刘赞娇 , 王天利 . Atherton-Todd反应的研究进展[J]. 有机化学, 2023 , 43(3) : 1069 -1083 . DOI: 10.6023/cjoc202210032
Phosphoramides or phosphates and their derivatives are a very important class of phosphorus-containing organic molecules, which are widely applied in medicinal chemistry, material chemistry and organic catalysis. As one of the most effective methods towards constructing phosphorus compounds, the Atherton-Todd reaction involves in situ halogenation of P(O)-H molecules with tetrachloromethane to generate the key intermediates of phosphoryl chlorides in the presence of bases, which subsequently react with amines or alcohols to form the corresponding phosphoramide or phosphate products. In recent years, this reaction has been widely explored by synthetic chemists due to its ease of operation, high atom economy, broad substrate versatility, and ease of incorporation of phosphorus units into active structural fragments. The research progress of the Atherton-Todd reaction and its application in organic synthesis in recent decades are summarized, and a brief outlook on the current research challenges is put forward, hoping to provide reference and thinking for the further development of the Atherton-Todd reaction.
| [1] | Kannan, P.; Kishore, K. Polymer 1992, 33, 418. |
| [2] | Orsini, F.; Sello, G.; Sisti, M. Curr. Med. Chem. 2010, 17, 264. |
| [3] | Joachimiak, ?.; B?a?ewska, K. M. J. Med. Chem. 2018, 61, 8536. |
| [4] | Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029. |
| [5] | Dutartre, M.; Bayardon, J.; Jugé, S. Chem. Soc. Rev. 2016, 45, 5771. |
| [6] | Kiss, N. Z.; Keglevich, G. Curr. Org. Chem. 2014, 18, 2673. |
| [7] | Atherton, F. R.; Openshaw, H. T.; Todd, A. R. J. Chem. Soc. 1945, 660. |
| [8] | Atherton, F. R.; Todd, A. R. J. Chem. Soc. 1947, 674. |
| [9] | Cao, S.; Zhao, Y. Sci. China: Chem. 2015, 45, 283. |
| [10] | Le Corre, S. S.; Berchel, M.; Couthon-Gourvès, H.; Haelters, J.-P.; Jaffrès. P.-A. Beilstein J. Org. Chem. 2014, 10, 1166. |
| [11] | Georgiev, E.; Roundhill, D. M.; Troev, K. Inorg. Chem. 1992, 31, 1965. |
| [12] | Steinberg, G. M. J. Org. Chem. 1950, 637. |
| [13] | Krutikov, V. I.; Erkin, A. V.; Krutikova, V. V. Russ. J. Gen. Chem. 2012, 82, 822. |
| [14] | Kong, A.; Engel, R. Bull. Chem. Soc. Jpn. 1985, 58, 3671. |
| [15] | Troev, K.; Kirilov, E. M. G.; Roundhill, D. M. Bull. Chem. Soc. Jpn. 1990, 63, 1284. |
| [16] | Georgiev, E. M.; Kaneti, J.; Troev, K.; Roundhill, D. M. J. Am. Chem. Soc. 1993, 115, 10964. |
| [17] | Liu, L.; Li, G.; Zeng, X.; Fu, L.; Cao, R. Heteroat. Chem. 1996, 7, 131. |
| [18] | Ashmus, R. A.; Lowary, T. L. Org. Lett. 2014, 16, 2518. |
| [19] | Tan, Y.; Han, Y.-P.; Zhang, Y.; Zhang, H.-Y.; Zhao, J.; Yang, S.-D. J. Org. Chem. 2022, 87, 3254. |
| [20] | Brands, K. M. J.; Wiedbrauk, K.; Williams, J. M.; Dolling, U.-H.; Reider, P. J. Tetrahedron Lett 1998, 39, 9583. |
| [21] | Dhineshkumar, J.; Prabhu, K. R. Org. Lett. 2013, 15, 6062. |
| [22] | Dar, B. A.; Dangroo, N. A.; Gupta, A.; Wali, A.; Khuroo, M. A.; Vishwakarma, R. A.; Singh, B. Tetrahedron Lett 2014, 55, 1544. |
| [23] | Anitha, T.; Ashalu, K. C.; Sandeep, M.; Mohd, A.; Wencel-Delord, J.; Colobert, F.; Reddy, K. R. Eur. J. Org. Chem. 2019, 2019, 7463. |
| [24] | Wang, X.; Ou, Y.; Peng, Z.; Yu, G.; Huang, Y.; Li, X.; Huo, Y.; Chen, Q. J. Org. Chem. 2019, 84, 14949. |
| [25] | Tan, C.; Liu, X.; Jia, H.; Zhao, X.; Chen, J.; Wang, Z.; Tan, J. Chem.-Eur. J. 2020, 26, 881. |
| [26] | Chen, Q.; Zeng, J.; Yan, X.; Huang, Y.; Wen, C.; Liu, X.; Zhang, K. J. Org. Chem. 2016, 81, 10043. |
| [27] | Kaboudin, B.; Donyavi, A.; Kazemi, F. Synthesis 2018, 50, 170. |
| [28] | Wang, Y.; Qian, P.; Su, J.-H.; Li, Y.; Bi, M.; Zha, Z.; Wang, Z. Green Chem. 2017, 19, 4769. |
| [29] | Li, Q.-Y.; Swaroop, T. R.; Hou, C.; Wang, Z.-Q. Pan, Y.-M.; Tang, H.-T. Adv. Synth. Catal. 2019, 361, 1761. |
| [30] | Deng, L.; Wang, Y.; Mei, H. Pan, Y.; Han, J. J. Org. Chem. 2019, 84, 949. |
| [31] | Dong, X.; Wang, R.; Jin, W.; Liu, C. Org. Lett. 2020, 22, 3062. |
| [32] | Li, Y.; Yang, Q.; Yang, L.; Lei, N.; Zheng, K. Chem. Commun. 2019, 55, 4981. |
| [33] | Wang, P.; Tang, S.; Huang, P.; Lei, A. Angew. Chem., Int. Ed. 2017, 56, 3009. |
| [34] | Huang, P.; Wang, P.; Tang, S.; Fu, Z.; Lei, A. Angew. Chem., Int. Ed. 2018, 57, 8115. |
| [35] | Li, C.-Y.; Liu, Y.-C.; Li, Y.-X.; Reddy, D. M.; Lee, C.-F. Org. Lett. 2019, 21, 7833. |
| [36] | Jin, X.; Yamaguchi, K.; Mizuno, N. Org. Lett. 2013, 15, 418. |
| [37] | Fraser, J.; Wilson, L. J.; Blundell, R. K.; Hayes, C. J. Chem. Commun. 2013, 49, 8919. |
| [38] | Zhou, Y.; Yin, S.; Gao, Y.; Zhao, Y.; Goto, M.; Han L.-B. Angew. Chem., Int. Ed. 2010, 49, 6852. |
| [39] | Li, C.; Chen, T.; Han, L.-B. Dalton Trans. 2016, 45, 14893. |
| [40] | Zhu, Y.; Chen, T.; Li, S.; Shimada, S.; Han, L.-B. J. Am. Chem. Soc. 2016, 138, 5825. |
| [41] | Xue, J.-W.; Zeng, M.; Zhang, S.; Chen, Z.; Yin, G. J. Org. Chem. 2019, 84, 4179. |
| [42] | Zhang, H.; Zhan, Z.; Lin, Y.; Shi, Y.; Li, G.; Wang, Q.; Deng, Y.; Hai, L.; Wu, Y. Org. Chem. Front. 2018, 5, 1416. |
| [43] | Pitre, S. P.; McTiernan, C. D.; Ismaili, H.; Scaiano, J. C. J. Am. Chem. Soc. 2013, 135, 13286. |
| [44] | Sun, J.-G.; Yang, H.; Li, P.; Zhang, B. Org. Lett. 2016, 18, 5114. |
| [45] | Fu, Y.; Duan, F.; Du, Z. Asian J. Org. Chem. 2021, 10, 1071. |
| [46] | Song, S.; Zhang, Y.; Yeerlan, A.; Zhu, B.; Liu, J.; Jiao, N. Angew. Chem., Int. Ed. 2017, 56, 2487. |
| [47] | Ou, Y.; Huang, Y.; He, Z.; Yu, G.; Huo, Y.; Li, X.; Gao, Y.; Chen, Q. Chem. Commun. 2020, 56, 1357. |
| [48] | Handoko.; Benslimane, Z.; Arora, P. S. Org. Lett. 2020, 22, 5811. |
| [49] | Yu, X.; Zhang, S.; Jiang, Z.; Zhang, H.-S.; Wang, T. Eur. J. Org. Chem. 2020, 3110. |
| [50] | Reiff, L. P.; Aaron, H. S. J. Am. Chem. Soc. 1970, 92, 5275. |
| [51] | Stec, W.; Mikolajczyk, M. Tetrahedron 1973, 29, 539. |
| [52] | Wang, G.; Shen, R.; Xu, Q.; Goto, M.; Zhao, Y.; Han, L-B. J. Org. Chem. 2010, 75, 3890. |
| [53] | Zhou, Y.; Wang, G.; Saga, Y.; Shen, R.; Goto, M.; Zhao, Y.; Han, L.-B. J. Org. Chem. 2010, 75, 7924. |
| [54] | Xiong, B.; Zhou, Y.; Zhao, C.; Goto, M.; Yin, S.-F.; Han, L.-B. Tetrahedron 2013, 69, 9373. |
| [55] | Cao, S.; Guo, Y.; Wang, J.; Qi, L.; Gao, P.; Zhao, H.; Zhao, Y. Tetrahedron Lett 2012, 53, 6302. |
| [56] | Cao, S.; Gao P, Guo, Y.; Zhao, H.; Wang, J.; Liu, Y.; Zhao, Y. J. Org. Chem. 2013, 78, 11283. |
| [57] | Kenner, G. W.; Williams, N. R. J. Chem. Soc. 1955, 522. |
| [58] | Lu, D.; Meng, Z.; Thakur, G. A.; Fan, P.; Steed, J.; Tartal, C. L.; Hurst, D. P.; Reggio, P. H.; Deschamps, J. R.; Parrish, D. A.; George, C.; J?rbe, T. U. C.; Lamb, R. J.; Makriyannis, A. J. Med. Chem. 2005, 48, 4576. |
| [59] | Chopa, A. B.; Lockhart, M. T.; Dorn, V. B. Organometallics 2002, 21, 1425. |
| [60] | Carsten, B.; He, F.; Son, H. J.; Xu, T.; Yu, L. Chem. Rev. 2011, 111, 1493. |
| [61] | Chen, H.; Huang, Z.; Hu, X.; Tang, G.; Xu, P.; Zhao, Y.; Cheng, C.-H. J. Org. Chem. 2011, 76, 2338. |
| [62] | Dutartre, M.; Bayardon, J.; Juge, S. Chem. Soc. Rev. 2016, 45, 5771. |
| [63] | Ni, H.; Chan, W.-L.; Lu, Y. Chem. Rev. 2018, 118, 9344. |
| [64] | Melvin, L. S. Tetrahedron Lett. 1981, 22, 3375. |
| [65] | Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984. |
| [66] | Mohd, A.; Anitha, T.; Reddy, K. R.; Wencel-Delord, J.; Colobert, F. Eur. J. Org. Chem. 2019, 7836. |
| [67] | Gatineau, D.; Nguyen, D. H.; Hérault, D.; Vanthuyne, N.; Leclaire, J.; Giordano, L.; Buono, G. J. Org. Chem. 2015, 80, 4132. |
| [68] | Fang, S.; Tan, J.-P.; Pan, J.; Zhang, H.; Chen, Y.; Ren, X.; Wang, T. Angew. Chem., Int. Ed. 2021, 60, 14921. |
| [69] | M?der, P.; Kattner, L. J. Med. Chem. 2020, 63, 14243. |
| [70] | Otocka, S.; Kwiatkowska, M.; Madalińska, L.; Kie?basiński, P. Chem. Rev. 2017, 117, 4147. |
| [71] | Fang, S.; Liu, Z.; Zhang, H.; Pan, J.; Chen, Y.; Ren, X.; Wang, T. ACS Catal. 2021, 11, 13902. |
/
| 〈 |
|
〉 |
