Chinese Journal of Organic Chemistry >
Synthesis of Terminal Vinyl Phosphine Oxides via Desulfonative C—P Formation from Alkenyl Sulfonium Salts
Received date: 2024-05-29
Revised date: 2024-07-20
Online published: 2024-08-19
Supported by
National Natural Science Foundation of China(22171249); National Natural Science Foundation of China(22071222)
Cesium carbonate was used as a base to achieve the desulfurization reaction of alkenyl sulfonium salts and phosphine oxides at room temperature, forming C(sp2)—P bonds. This method features simple operation, mild reaction conditions, and good functional group compatibility, offering a straightforward and efficient preparation route for terminal vinyl phosphine oxides.
Jiangzhen An , Qiyan Lv , Kai Sun , Xiaolan Chen , Lingbo Qu , Bing Yu . Synthesis of Terminal Vinyl Phosphine Oxides via Desulfonative C—P Formation from Alkenyl Sulfonium Salts[J]. Chinese Journal of Organic Chemistry, 2024 , 44(12) : 3747 -3752 . DOI: 10.6023/cjoc202405043
| [1] | Ma C.; Li X.; Chen X.; He X.; Zhang S.-T.; Jiang Y.-Q.; Yu B. Org. Lett. 2023, 25, 8016. |
| [2] | Zhang Y.; Guo Y.; Zhao Y.; Cao S. J. Org. Chem. 2024, 89, 3259. |
| [3] | Tang J.; Hu J.; Zhu Z.; Pu S. Chin. J. Org. Chem. 2023, 43, 4036 (in Chinese). |
| [3] | (汤娟, 胡家榆, 祝志强, 蒲守智, 有机化学, 2023, 43, 4036.) |
| [4] | Asok N.; Gaffen J. R.; Baumgartner T. Acc. Chem. Res. 2023, 56, 536. |
| [5] | Vil’ V. A.; Igor B. K.; Terent’ev A. O. Sci. China: Chem. 2021, 64, 681. |
| [6] | Zhang J.-Q.; Yang S.; Han L.-B. Tetrahedron Lett. 2020, 61, 151556. |
| [7] | Ge H.; Song W.; Peng X.; Wang H.; Jiang J. J. Liaocheng Univ. (Nat. Sci. Ed.) 2022, 35, 98 (in Chinese). |
| [7] | (葛会成, 宋文科, 彭珣, 王海涛, 江吉周, 聊城大学学报(自然科学版), 2022, 35, 98.) |
| [8] | Li Z.; Zhou W.; Yu M.; Wu X.; Huang Z.; Lü K. J. Liaocheng Univ. (Nat. Sci. Ed.) 2024, 37, 50 (in Chinese). |
| [8] | (李舟, 周维创, 虞梦雪, 伍晓锋, 黄子宾, 吕康乐, 聊城大学学报(自然科学版) 2024, 37, 50.) |
| [9] | Yu B.; Zeng F. L. J. Henan Normal Univ. (Nat. Sci. Ed.) 2024, 52, 10 (in Chinese). |
| [9] | (於兵, 曾繁林, 河南师范大学学报(自然科学版), 2024, 52, 10.) |
| [10] | Fang S. Q.; Liu Z. J.; Wang T. L. Chin. J. Org. Chem. 2023, 43, 1069 (in Chinese). |
| [10] | (方思强, 刘赞娇, 王天利, 有机化学, 2023, 43, 1069.) |
| [11] | Wang Q.; Meng Y.; Wu L.; Li E.-Q. Chin. Chem. Lett. 2023, 34, 108544. |
| [12] | Ono Y.; Han L. B. Tetrahedron Lett. 2006, 47, 421. |
| [13] | Sulzer-Mossé S.; Tissot M.; Alexakis A. Org. Lett. 2007, 9, 3749. |
| [14] | Rabasso N.; Fadel A. Tetrahedron Lett. 2010, 51, 60. |
| [15] | Nagata S.; Kawaguchi S.-I.; Matsumoto M.; Kamiya I.; Nomoto A.; Sonoda M.; Ogawa A. Tetrahedron Lett. 2007, 48, 6637. |
| [16] | Liu L.; Liu M.; Liu B.; Wang Q.; Li Y.; Feng K.; Qiu R.; Zhou Y. Tetrahedron Lett. 2023, 133, 154823. |
| [17] | Wang H.; Li Y.; Tang Z.; Wang S.; Zhang H.; Cong H.; Lei A. ACS Catal. 2018, 8, 10599. |
| [18] | Wang T.; Chen S.; Shao A.; Gao M.; Huang Y.; Lei A. Org. Lett. 2015, 17, 118. |
| [19] | Guo H. M.; Zhou Q. Q.; Jiang X.; Shi D. Q.; Xiao W. J. Adv. Synth. Catal. 2017, 359, 4141. |
| [20] | Castoldi L.; Rajkiewicz A. A.; Olofsson B. Chem. Commun. 2020, 56, 14389. |
| [21] | Li X.; Jiang M.; Zuo J.; Song X.; Lv J.; Yang D. Sci. China: Chem. 2023, 66, 791-798. |
| [22] | Zhao H.; Cuomo V. D.; Rossi-Ashton J. A.; Procter D. J. Chem 2024, 10, 1240. |
| [23] | Dewanji A.; van Dalsen L.; Rossi-Ashton J. A.; Gasson E.; Crisenza G. E. M.; Procter D. J. Nat. Chem. 2023, 15, 43. |
| [24] | Li J.; Chen J.; Sang R.; Ham W.-S.; Plutschack M. B.; Berger F.; Chabbra S.; Schnegg A.; Genicot C.; Ritter T. Nat. Chem. 2020, 12, 56. |
| [25] | Meng H.; Liu M.-S.; Shu W. Chem. Sci. 2022, 13, 13690. |
| [26] | Sun K.; Shi A.; Liu Y.; Chen X.; Xiang P.; Wang X.; Qu L.; Yu B. Chem. Sci. 2022, 13, 5659. |
| [27] | Xu H.; Zhang J.; Zuo J.; Wang F.; Lv J.; Hun X.; Yang D. Chin. J. Org. Chem. 2022, 42, 4037 (in Chinese). |
| [27] | (徐浩, 张杰, 左峻泽, 王丰晓, 吕健, 混旭, 杨道山, 有机化学, 2022, 42, 4037.) |
| [28] | Kozhushkov S. I.; Alcarazo M. Eur. J. Inorg. Chem. 2020, 2020, 2486. |
| [29] | Nenajdenko V. G.; Vertelezkij P. V.; Gridnev I. D.; Shevchenko N. E.; Balenkova E. S. Tetrahedron 1997, 53, 8173. |
| [30] | Mondal M.; Chen S.; Kerrigan N. J. Molecules 2018, 23, 738. |
| [31] | Zhang Y.-L.; Yang L.; Wu J.; Zhu C.; Wang P. Org. Lett. 2020, 22, 7768. |
| [32] | Kong X.; Chen Y.; Liu Q.; Wang W.; Zhang S.; Zhang Q.; Chen X.; Xu Y.-Q.; Cao Z.-Y. Org. Lett. 2023, 25, 581. |
| [33] | Ge C.; Qiao L.; Zhang Y.; Sun K.; An J.; Peng M.; Chen X.; Qu L.; Yu B. Chin. J. Chem. 2024, 42, 1679. |
| [34] | Liu M.-S.; Du H.-W.; Meng H.; Xie Y.; Shu W. Nat. Commun. 2024, 15, 529. |
| [35] | Jessop C. M.; Parsons A. F.; Routledge A.; Irvine D. J. Eur. J. Org. Chem. 2006, 2006, 1547. |
| [36] | Wang K.-L.; Ji H.-T.; Ou L.-J.; He W.-M. Eur. J. Org. Chem. 2023, 26, e202300752. |
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