BF3•Et2O促进的双烯酮-酚重排合成具有聚集诱导发光(AIE)效应的磷杂七元环化合物
收稿日期: 2022-04-06
修回日期: 2022-05-01
网络出版日期: 2022-05-18
基金资助
国家自然科学基金(22171245); 国家自然科学基金(22101262); 国家自然科学基金(21672193); 河南省科技攻关(202102310327); 郑州大学资助项目
BF3•Et2O Promoted Dienone-Phenol Type Rearrangement to Synthesize Phosphepine with Aggregation Induced Luminescence (AIE) Effect
Received date: 2022-04-06
Revised date: 2022-05-01
Online published: 2022-05-18
Supported by
National Natural Science Foundation of China(22171245); National Natural Science Foundation of China(22101262); National Natural Science Foundation of China(21672193); Key Scientific and Technological Project of Henan Province(202102310327); Zhengzhou University
磷杂环庚三烯类化合物作为一类新兴的发光分子吸引了人们研究的兴趣. 因其合成路线非常有限, 对其结构与发光性能相关性的探索还远远落后于相应的磷杂五、六元环类化合物. 双烯酮化合物在酸或碱的促进下发生重排反应被广泛用于酚类化合物的制备. 利用螺环双烯酮磷杂六元环化合物在BF3•Et2O作用下发生双烯酮-酚重排反应合成了一系列具有聚集诱导发光(AIE)效应的磷杂七元环化合物.
关键词: 双烯酮-酚重排反应; 磷杂七元环; 聚集诱导发光(AIE); BF3•Et2O
郭泽 , 吴迪 , 王丽丽 , 段征 . BF3•Et2O促进的双烯酮-酚重排合成具有聚集诱导发光(AIE)效应的磷杂七元环化合物[J]. 有机化学, 2022 , 42(8) : 2481 -2487 . DOI: 10.6023/cjoc202204012
Very recently, phosphepines has emerged as a new luminogen. Further explorations of this new motif in optical materials have been hampered by the lack of general and practical methods for their synthesis and derivation. The rearrangement of dienones promoted by acid or base is widely used in the preparation of phenols. A series of phosphepines with aggregation induced luminescence (AIE) effect were synthesized by the dienone-phenol rearrangement reaction of spirodienone six-membered phosphacycles in the presence of BF3•Et2O.
| [1] | (a) Ni, H.; Chan, W. L.; Lu, Y. Chem Rev. 2018, 118, 9344. |
| [1] | (c) Hirai, M.; Tanaka, N.; Sakai, M.; Yamaguchi, S. Chem. Rev. 2019, 119, 8291. |
| [2] | (a) Baumgartner, T. Acc. Chem. Res. 2014, 47, 1613. |
| [2] | (b) Baumgartner, T.; Réau, R. Chem. Rev. 2006, 106, 4681. |
| [2] | (c) Wang, L.; Tian, R.; Duan, Z.; Mathey, F. Chin. J. Org. Chem. 2013, 33, 36. (in Chinese) |
| [2] | (王丽丽, 田荣强, 段征, François, Mathey, 有机化学, 2013, 33, 36.) |
| [2] | (d) Shameem, M. A.; Orthaber, A. Chem.-Eur. J. 2016, 22, 10718. |
| [2] | (e) Duffy, M. P.; Delaunay, W.; Bouit, P. A.; Hissler, M. Chem. Soc. Rev. 2016, 45, 5296. |
| [2] | (g) Regulska, E.; Romero-Nieto, C. Dalton Trans. 2018, 47, 10344. |
| [3] | (a) Yasuike, S.; Kiharada, T.; Tsuchiya, T.; Kurita, J. Chem. Pharm. Bull. 2003, 51, 1283. |
| [3] | (b) Kurita, J.; Shiratori, S.; Yasuike, S.; Tsuchiya, T. J. Chem. Soc., Chem. Commun. 1991, 17, 1227. |
| [3] | (c) Yasuike, S.; Ohta, H.; Shiratori, S.; Kurita, J.; Tsuchiya, T. J. Chem. Soc., Chem. Commun. 1993, 24, 1817. |
| [3] | (d) Märkl, G.; Burger, W. Tetrahedron Lett. 1983, 24, 2545. |
| [4] | (a) Wang, L.; Ma, J.; Si, E.; Duan, Z. Synthesis 2020, 53, 623. |
| [4] | (b) Ren, Y.; Sezen, M.; Guo, F.; Jäkle, F.; Loo, Y. L. Chem. Sci. 2016, 7, 4211. |
| [5] | (a) Yasuike, S.; Nakashima, F.; Kurita, J.; Tsuchiya, T. Heterocycles 1997, 10, 1899. |
| [5] | (b) Lyaskovskyy, V.; van Dijk-Moes, R. J. A.; de Bruin, B.; Lammertsma, K. Organometallics 2012, 32, 363. |
| [5] | (c) Padberg, K.; Ascherl, J. D. R.; Kivala, M. Chem.-Eur. J. 2020, 26, 3474. |
| [6] | Delouche, T.; Bouit, P. A.; Hissler, M. Org. Lett. 2019, 21, 802. |
| [7] | (a) Delouche, T.; Roisnel, T.; Dorcet, V.; Hissler, M.; Bouit, P. A. Eur. J. Inorg. Chem. 2021, 2021, 1082. |
| [7] | (b) Delouche, T.; Bouit, P. A. Chem.-Eur. J. 2020, 26, 1856. |
| [8] | Wu, D.; Hu, C.; Duan, Z. Eur. J. Org. Chem. 2019, 2019, 6369. |
| [9] | (a) Hegan, D. C.; Lu, Y.; Glazer, P. M. Proc. Natl. Acad. Sci. U. S. A. 2010, 107, 2201. |
| [9] | (b) Wilds, A.; Djerassi, C. J. Am. Chem. Soc. 1946, 68, 1715. |
| [10] | (a) Fenton, S.; Arnold, R.; Fritz, H. J. Am. Chem. Soc. 1955, 77, 5983. |
| [10] | (b) Burnell, R.; Taylor, W. J. Chem. Soc. 1954, 3486. |
| [10] | (c) Taylor, E. C.; Andrade, J. G.; Rall, G. J.; McKillop, A. J. Am. Chem. Soc. 1980, 102, 6513. |
| [11] | Moisan, L.; Wagner, M.; Comesse, S.; Doris, E. Tetrahedron Lett. 2006, 47, 9093. |
| [12] | Guo, X.; Xing, Q.; Lei, K.; Zhang-Negrerie, D.; Du, Y.; Zhao, K. Adv. Synth. Catal. 2017, 359, 4393. |
| [13] | Jumbam, N. D.; Maganga, Y.; Mtwa, S. Molecules 2019, 24, 3720. |
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