协同的非均相光氧化还原催化和镍催化构建碳磷键

引用本文: Koranteng Ernest, 刘以银, 刘思跃, 伍强贤, 陆良秋, 肖文精. 协同的非均相光氧化还原催化和镍催化构建碳磷键[J]. 催化学报, 2019, 40(12): 1841-1846. doi: S1872-2067(19)63379-6 shu

Citation: Ernest Koranteng, Yi-Yin Liu, Si-Yue Liu, Qiang-Xian Wu, Liang-Qiu Lu, Wen-Jing Xiao. Practical C-P bond formation via heterogeneous photoredox and nickel synergetic catalysis[J]. Chinese Journal of Catalysis, 2019, 40(12): 1841-1846. doi: S1872-2067(19)63379-6 shu

协同的非均相光氧化还原催化和镍催化构建碳磷键

a 华中师范大学化学学院, 农药与化学生物学重点实验室, 华师-渥太华大学国际联合研究中心, 湖北武汉 430079;
b 中国科学院兰州化学物理研究所, 羰基合成与选择氧化国家重点实验室, 甘肃兰州 730000
基金项目:
国家自然科学基金（21822103，21820102003，21772052，21772053，21572074，21472057）；高等学校学科创新引智计划（B17019）；湖北省自然科学基金（2017AHB047）.

摘要: 作为一类重要的功能有机分子，有机膦化合物广泛用于医药、农药、材料以及生命科学等众多领域中.因此，实现C-P键的高效、高选择性构建一直是合成化学家们的一项重要研究内容.过渡金属催化的碳磷成键反应为有机磷化物的合成提供了一个行之有效的方法，芳基卤代物、硼酸、三氟磺酸酯等前体均可用于该偶联反应.但是，这些反应往往需要用到价格昂贵、空气敏感的金属催化剂或配体以及当量的氧化试剂，且反应条件苛刻.为此，人们迫切需要发展经济、高效、条件温和且具有普适性的绿色合成方法来解决有机膦化合物合成领域的这一难点问题.
近年来，可见光促进的光氧化还原催化因其绿色、环保的优点而受到越来越多合成化学家们的关注.目前，所使用的光催化剂大多是基于贵金属钌、铱的金属有机络合物或一些有机染料分子.相比于均相催化的有机光化学反应，非均相催化过程在催化剂的稳定性与回收利用以及产物分离等方面具有明显的优势.
本文使用商业可得的半导体材料硫化镉作为非均相光催化剂，金属镍复合物作为过渡金属催化剂，实现了过渡金属与光敏剂协同催化的碳磷成键反应.该反应具有非常广的底物适用范围，芳基氯代物、溴代物、三氟磺酸酯以及烯基溴代物均能较好地参与该反应，温和条件下高效地合成得到一系列有机磷化物.将反应规模扩大至克级时，我们发现反应效率几乎不受影响，且反应结束后过滤得到的光催化剂在循环5次后反应效果仍相近.由此可见硫化镉/镍非均相催化体系在有机膦化合物的光化学合成中的有效性和实用性.此外，我们还通过控制实验和自由基捕获实验以及相关文献，提出了该反应的可能机理.

关键词:

English

Practical C-P bond formation via heterogeneous photoredox and nickel synergetic catalysis

a CCNU-uOttawa Joint Research Centre, Hubei International Scientific and Technological Cooperation Base of Pesticide and Green Synthesis, Key Laboratory of Pesticides & Chemical Biology Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, Hubei, China;
b State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000, Gansu, China
Received Date: 19 April 2019
Revised Date: 11 May 2019
Fund Project:
We are grateful to the National Science Foundation of China (21822103, 21820102003, 21772052, 21772053, 21572074, 21472057), the Program of Introducing Talents of Discipline to Universities of China (111 Program, B17019), the Natural Science Foundation of Hubei Province (2017AHB047), and the International Joint Research Center for Intelligent Biosensing Technology and Health for support of this research.

Abstract: An efficient C-P bond formation reaction was developed by virtue of the synergetic catalysis strategy by merging heterogeneous photocatalysis and nickel catalysis. This platform utilizing cadmium sulfide semiconductors as heterogeneous photocatalysts and nickel complexes as transition metal catalysts provided a variety of organophosphorus compounds from readily available aryl and vinyl halides, as well as aryl triflates, with generally a good-to-excellent reaction efficiency (31 examples, 46%-98% yields). The current protocol features mild reaction conditions, a broad substrate scope, recyclability of photocatalysts, and inexpensive catalysts, thus defining the practical and economic proprieties of the present catalyst system.

Key words:

Photoredox catalysis
/ Nickel catalysis
/ Construction of carbon-phosphorus bond
/ Heterogeneous

1. [1] L. D. Quin, A Guide to Organophosphorus Chemistry; Wiley Interscience, New York, 2000.
2. [2] P. J. Murphy, Organophosphorus Reagents, Oxford University Press, Oxford, U.K., 2004.
3. [3] T. Baumgartner, R. Reau, Chem. Rev., 2006, 106, 4681-4727.
4. [4] P. Guga, Curr. Top. Med. Chem., 2007, 7, 695-713.
5. [5] R. Martin, S. L. Buchwald, Acc. Chem. Res., 2008, 41, 1461-1473.
6. [6] C. S. Demmer, N. Krogsgaard-Larsen, L. Bunch, Chem. Rev., 2011, 111, 7981-800.
7. [7] G. P. Horsman, D. L. Zechel, Chem. Rev., 2017, 117, 5704-5783.
8. [8] T. Hirao, T. Masunaga, Y. Ohshiro, T. Agawa, Tetrahedron Lett., 1980, 21, 3595-3598.
9. [9] T. Hirao, T. Masunaga, Y. Ohshiro, T. Agawa, Synthesis, 1981, 56-57.
10. [10] T. Hirao, T. Masunaga, N. Yamada, Y. Ohshiro, T. Agawa, Bull. Chem. Soc. Jpn., 1982, 55, 909-913.
11. [11] J. L. Montchamp, Y. R. Dumond, J. Am. Chem. Soc., 2001, 123, 510-511.
12. [12] K. Muñiz, Angew. Chem. Int. Ed., 2009, 48, 9412-9423.
13. [13] T. Chen, J. S. Zhang, L. B. Han, Dalton Trans., 2016, 45, 1843-1849.
14. [14] D. Gelman, L. Jiang, S. L. Buchwald, Org. Lett., 2003, 5, 2315-2318.
15. [15] C. R. Shen, G. Q. Yang, W. B. Zhang, Org. Biomol. Chem., 2012, 10, 3500-3505.
16. [16] P. Xu, Z. Wu, N. Zhou, C. Zhu, Org. Lett., 2016, 18, 1143-1145.
17. [17] J. M. R. Narayanam, C. R. J. Stephenson, Chem. Soc. Rev., 2011, 40, 102-113.
18. [18] J. Xuan, W.-J. Xiao, Angew. Chem. Int. Ed., 2012, 51, 6828-6838.
19. [19] D. M. Schultz, T. P. Yoon, Science, 2014, 343, 985-993.
20. [20] C. K. Prier, D. A. Rankic, D. W. C. MacMillan, Chem. Rev., 2013, 113, 5322-5363.
21. [21] N. A. Romero, D. A. Nicewicz, Chem. Rev., 2016, 116, 10075-10166.
22. [22] L. Marzo, S. K. Pagire, O. Reiser, B. König, Angew. Chem. Int. Ed., 2018, 57, 10034-10072.
23. [23] K. Luo, W.-C. Yang, L. Wu, Asian J. Org. Chem., 2017, 6, 350-367.
24. [24] K. Luo, Y.-Z. Chen, L.-X. Chen, L. Wu, J. Org. Chem., 2016, 81, 4682-4689.
25. [25] P. Peng, L. Peng, G. Wang, F. Wang, Y. Luo, A. Lei, Org. Chem. Front., 2016, 3, 749-752.
26. [26] R. S. Shaikh, S. J. S. Düsel, B. König, ACS Catal., 2016, 6, 8410-8414.
27. [27] J. Yuan, W.-P. To, Z.-Y. Zhang, C.-D. Yue, S. Meng, J. Chen, Y. Liu, G.-A. Yu, C.-M. Che, Org Lett., 2018, 20, 7816-7820.
28. [28] H. Zeng, Q. Dou, C.-J. Li, Org Lett., 2019, 21, 1301-1305.
29. [29] Y. He, H. Wu, F. D. Toste, Chem. Sci., 2015, 6, 1194-1198.
30. [30] J. Xuan, T.-T. Zeng, J.-R. Chen, L.-Q. Lu, W.-J. Xiao, Chem. Eur. J., 2015, 21, 4962-4965.
31. [31] L. Niu, J. Liu, H. Yi, S. Wang, X.-A. Liang, A. K. Singh, C.-W. Chiang, A. Lei, ACS Catal., 2017, 7, 7412-7416.
32. [32] L-L. Liao, Y-Y. Gui, X-B. Zhang, G. Shen, H-D. Liu, W-J. Zhou, J. Li, D-G. Yu, Org. Lett., 2017, 19, 3735-3738.
33. [33] M. N. Hopkinson, B. Sahoo, J.-L. Li, F. Glorius, Chem. Eur. J., 2014, 20, 3874-3886.
34. [34] K. L. Skubi, T. R. Blum, T. P. Yoon, Chem. Rev., 2016, 116, 10035-10074.
35. [35] J. Twilton, C. Le, P. Zhang, M. H. Shaw, R. W. Evans, D. W. C. MacMillan, Nat. Rev. Chem., 2017, 1, 0052.
36. [36] F. Wang, W. G. Wang, X. J. Wang, H. Y. Wang, C. H. Tung, L. Z. Wu, Angew. Chem. Int. Ed., 2011, 50, 3193-3197.
37. [37] S. Ma, J. Xie, J. Wen, K. He, X. Li, W. Liu, X. Zhang, Appl. Surf. Sci., 2017, 391, 580-591.
38. [38] J. Feng, H. Frei, Angew. Chem. Int. Ed., 2009, 48, 1841-1844.
39. [39] W. J. Youngblood, S. H. A. Lee, K. Maeda, T. E. Mallouk, Acc. Chem. Res., 2009, 42, 1966-1973.
40. [40] A. Kumar, A. G. Samuelson, Eur. J. Org. Chem., 2011, 951-959.
41. [41] U. P. Apfel, W. Weigand, Angew. Chem. Int. Ed., 2011, 50, 4262-4264.
42. [42] R. Lechner, B. König, Synthesis, 2010, 1712-1718.
43. [43] X. J. Lang, H. W. Ji, C. C. Chen, W. H. Ma, J. C. Zhao, Angew. Chem. Int. Ed., 2011, 50, 3934-3937.
44. [44] T. Mitkina, C. Stanglmair, W. Setzer, M. Gruber, H. Kischc, B. König, Org. Biomol. Chem., 2012, 10, 3556-3561.
45. [45] J.-R. Chen, X.-Q. Hu, L.-Q. Lu, W.-J. Xiao, Acc. Chem. Res., 2016, 49, 1911-1923.
46. [46] W. Ding, L.-Q. Lu, Q.-Q. Zhou, Y. Wei, J.-R. Chen, W.-J. Xiao, J. Am. Chem. Soc., 2017, 139, 63-66.
47. [47] M.-M. Li, Y. Wei, J. Liu, H.-W. Chen, L.-Q. Lu, W.-J. Xiao, J. Am. Chem. Soc., 2017, 139, 14707-14713.
48. [48] Q.-Q. Zhou, D. Liu, W.-J. Xiao, L.-Q. Lu, Acta Chim. Sinica, 2017, 75, 110-114.
49. [49] Y. Wei, S. Liu, M.-M. Li, Y. Li, Y. Lan, L.-Q. Lu, W.-J. Xiao, J. Am. Chem. Soc., 2019, 141, 133-137.
50. [50] X. Jiang, M.-M. Zhang, W. Xiong, L.-Q. Lu, W.-J. Xiao, Angew. Chem. Int. Ed., 2019, 58, 2402-2406.
51. [51] Z. Chai, T.-T. Zeng, Q. Li, L.-Q. Lu, W.-J. Xiao, D. Xu, J. Am. Chem. Soc., 2016, 138, 10128-10131.
52. [52] T. Minami, J. Motoyoshiya, Synthesis, 1992, 4, 333-349.
53. [53] P. Adler, A. Fadel, N. Rabasso, Tetrahedron, 2014, 70, 4437-4456.
54. [54] X. Y. Jiao, W. G. Bentrude, J. Org. Chem., 2003, 68, 3303-3306.
55. [55] G. J. Schlichting, J. L. Horan, J. D. Jessop, S. E. Nelson, S. Seifert, Y. Yang, A. M. Herring, Macromolecules, 2012, 45, 3874-3882.
56. [56] Q. Wu, R. A. Weiss, Polymer, 2007, 48, 7558-7566.

扫一扫看文章

计量

PDF下载量: 13
文章访问数: 1339
HTML全文浏览量: 177

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

协同的非均相光氧化还原催化和镍催化构建碳磷键

English

Practical C-P bond formation via heterogeneous photoredox and nickel synergetic catalysis

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

计量

通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

协同的非均相光氧化还原催化和镍催化构建碳磷键

English

Practical C-P bond formation via heterogeneous photoredox and nickel synergetic catalysis

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

计量

文章相关

通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs