Citation: Ruan Liheng, Liu Chang, Sun Jing, Zhou Mingdong. Recent Advances on the Synthesis of β-Ketophosphine Oxides[J]. Chinese Journal of Organic Chemistry, ;2019, 39(9): 2403-2411. doi: 10.6023/cjoc201901027 shu

Recent Advances on the Synthesis of β-Ketophosphine Oxides

College of Chemistry, Chemical Engineering and Environment, Liaoning Shihua University, Fushun 113001

Corresponding author: Sun Jing, sunjing@lnpu.edu.cn Zhou Mingdong, mingdong.zhou@lnpu.edu.cn
Received Date: 17 January 2019
Revised Date: 15 April 2019
Available Online: 19 September 2019
Fund Project: Project supported by the Doctor Startup Fund of Liaoning Province (No. 20180540085)the Doctor Startup Fund of Liaoning Province 20180540085

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β-Ketophosphine oxides are extremely important phosphorus-containing compounds and widely utilitied in the field of organic synthesis chemistry. Developing simple, green and efficient protocol to synthesize β-ketophosphine oxides has attracted great attention of chemists in recent years. The recent advances on the synthesis of β-ketophosphine oxides via phosphorus-centered radical addition reaction or hydration reaction are summarized.
- β-ketophosphine oxide,
- phosphorus-centered radical,
- hydration reaction
1. [1]
  (a) Perumal, S. K.; Adediran, S. A.; Pratt, R. F. Bioorg. Med. Chem. 2008, 16, 6987.
  (b) Li, R.; Chen, X.; Wei, S.; Sun, K.; Fan, L.-L.; Liu, Y.; Qu, L.-B.; Zhao, Y.-F.; Yu, B. Adv. Synth. Catal. 2018, 360, 4807.
  (c) Muhammad, M.-H.; Chen, X.-L.; Yu, B.; Qu, L.-B.; Zhao, Y.-F. Pure Appl. Chem. 2019, 91, 33.
  (d) Jing, C.-F.; Chen, X.-L.; Sun, K.; Yang, Y.-K.; Chen, T.; Liu, Y.; Qu, L.-B.; Zhao, Y.-F.; Yu, B. Org. Lett. 2019, 21, 486.
  (e) Liu, Y.-L.; Liang, Y.; Pi, S.-F.; Li, J.-H. J. Org. Chem. 2009, 74, 5691.
  (f) Kondoh, A.; Yorimitsu, H.; Oshima, K. Chem.-Asian J. 2010, 5, 398.
  (g) Perumal, S.-K.; Adediran, S.-A.; Pratt, R.-F. Bioorg. Med. Chem. 2008, 16, 6987.
2. [2]
  (a) Yan, B.; Spilling, C.-D. J. Org. Chem. 2008, 73, 5385.
  (b) Pronin, S.-V.; Martinez, A.; Kuznedelov, K.; Severinov, K.; Shuman, H.-A.; Kozmin, S.-A. J. Am. Chem. Soc. 2011, 133, 12172.
  (c) Müller, S.; Mayer, T.; Sasse, F.; Maier, M.-E. Org. Lett. 2011, 13, 3940.
3. [3]
  (a) Ryglowski, A.; Kafarski, P. Tetrahedron 1996, 52, 10685.
  (b) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2931.
4. [4]
  McCabe, D.-J.; Duesler, E.-N.; Paine, R.-T. Inorg. Chem.1985, 24, 4626. doi: 10.1021/ic00220a040
5. [5]
  (a) Perumal, S.-K.; Adediran, S.-A.; Pratt, R.-F. Bioorg. Med. Chem. 2008, 16, 6987.
  (b) Nguyen, L. M.; Diep, V. V.; Phan, H. T.; Niesor E. J.; Masson D.; GuyonGellin, Y.; Buattini, E.; Severi, C.; Azoulay, R.; Bentzen, C. L. WO 2004026242, 2004.
  (c) Erion M. D.; Jiang, H.; Boyer, S. H. US 20060046980, 2006.
6. [6]
  (a) Arbuzov, B. A. Pure Appl. Chem. 1964, 9, 307.
  (b) Bhattacharya, A. K.; Thyagarajan, G. Chem. Rev. 1981, 81, 415.
7. [7]
  (a) Narkunan, K.; Nagarajan, M. J. Org. Chem. 1994, 59, 6386.
  (b) Maloney, K. M.; Chung, J. Y. L. J. Org. Chem. 2009, 74, 7574.
  (c) Robert, R. M.; Ken, M.; Johann, C.; Jason, T.; Robert, L.; Margaret, F. Tetrahedron Lett. 2009, 50, 870.
  (d) Demmer, C. S.; Krogsgaard-Larsen, N.; Bunch, L. Chem. Rev. 2011, 111, 7981.
8. [8]
  (a) Leca, D.; Fensterbank, L.; Lacote, E.; Malacria, M. Chem. Soc. Rev. 2005, 34, 858.
  (b) Marque, S.; Tordo, P. In New Aspects in Phosphorus Chemistry, 5th ed., Vol. 250, Ed.: Majoral, J. P., Springer, Berlin, Heidelberg, 2005, p. 43.
  (c) Baumgartner, T.; Réau, R. Chem. Rev. 2006, 106, 4681.
  (d) Xie, J.-H.; Zhou, Q.-L. Acc. Chem. Res. 2008, 41, 581.
9. [9]
  Zhang, P.-B.; Zhang, L.-L.; Gao, Y.-Z.; Xu, J.;Fang, H.;Tang, G.;Zhao Y.-F. Chem. Commun.2015, 51, 7839. doi: 10.1039/C5CC01904D
10. [10]
  Feng, S.-B.; Li, J.-L.; He, F.-F.; Li, T.;Li, H.-L.; Wang, X.-L.; Xie, X.-G.; She, X.-G. Org. Chem. Front.2019, 6, 946. doi: 10.1039/C9QO00006B
11. [11]
  Gutierrez, V.;Mascaro, E.;Alonso, F.;Moglie, Y.;Radivoy, G. RSC Adv.2015, 5, 65739. doi: 10.1039/C5RA10223E
12. [12]
  Zhong, W.-W.; Zhang, Q.;Li, M.-S.; Hu, D.-Y.; Cheng, M.;Du, F.-T.; Ji, J.-X.; Wei, W. Synth. Commun.2016, 46, 1377. doi: 10.1080/00397911.2016.1205196
13. [13]
  Chen, X.;Chen, X.;Li, X.;Qu, C.;Qu, L.;Bi, W.;Sun, K.;Zhao, Y.-F. Tetrahedron 2017, 73, 2439. doi: 10.1016/j.tet.2017.03.026
14. [14]
  Zeng, Y.-F.; Tan, D.-H.; Lv, W.-X.; Li, Q.-J.; Wang, H.-G. Eur. J. Org. Chem.2015, 4335.
15. [15]
  Chen, X.;Li, X.;Chen, X.-L.Qu, L.-B.; Chen, J.-Y.; Sun, K.;Liu, Z.-D.; Bi, W.-Z.; Xia, Y.-Y.; Wu, H.-T.; Zhao, Y.-F. Chem. Commun.2015, 51, 3846. doi: 10.1039/C4CC10312B
16. [16]
  Mi, X.;Wang, C.;Huang, M.;Zhang, J.;Wu, Y. Org. Lett.2014, 16, 3356. doi: 10.1021/ol5013839
17. [17]
  Wang, L.-J.; Wang, A.-Q.; Xia, Y.;Wu, X.-X.; Liu, X.-Y.; Liang, Y.-M. Chem. Commun.2014, 50, 13998. doi: 10.1039/C4CC06923D
18. [18]
  Zhou, Z.-Z.; Zheng, L.;Yan, X.-B.; Jin, D.-P.; He, Y.-T.; Liang, Y.-M. Org. Biomol. Chem.2016, 14, 4507. doi: 10.1039/C6OB00505E
19. [19]
  Liu, J.;Zhao, S.;Song, W.;Li, R.;Guo, X.;Zhuo, K.;Yue, Y. Adv. Synth. Catal.2017, 359, 609. doi: 10.1002/adsc.201600850
20. [20]
  Zhang, H.;Gu, Z.;Li, Z.;Pan, C.;Li, W.;Hu, H.;Zhu, C. J. Org. Chem.2016, 81, 2122. doi: 10.1021/acs.joc.5b01879
21. [21]
  Li, L.-L.; Huang, W.-B.; Chen, L.-J.; Dong, J.-X.; Ma, X.-B.; Peng, Y.-G. Angew. Chem., Int. Ed.2017, 56, 10539. doi: 10.1002/anie.201704910
22. [22]
  Yuan, J.-W.; Li, Y.-Z.; Mai, W.-P.; Yang, L.-R.; Qu, L.-B. Tetrahedron 2016, 72, 3084. doi: 10.1016/j.tet.2016.04.034
23. [23]
  Wei, W.;Ji, J.-X. Angew. Chem., Int. Ed.2011, 50, 9097. doi: 10.1002/anie.201100219
24. [24]
  Yang, X.-Y.; Du, F.-T.; Wei, W.;Ji, J.-X.; Chen, Q. Chin. J. Appl. Eviron. Biol.2015, 21, 263.
25. [25]
  Yi, N.-N.; Wang, R.-J.; Zou, H.-X.; He, W.-B.; Fu, W.-Q.; He, W.-M. J. Org. Chem.2015, 80, 5023. doi: 10.1021/acs.joc.5b00408
26. [26]
  Zhou, M.-X.; Zhou, Y.;Song, Q.-L. Chem.-Eur. J.2015, 21, 10654. doi: 10.1002/chem.201501226
27. [27]
  Zhou, M.-X.; Chen, M.;Zhou, Y.;Yang, K.;Su, J.-H.; Du, J.-F.; Song, Q.-L. Org. Lett.2015, 17, 1786. doi: 10.1021/acs.orglett.5b00574
28. [28]
  Zhou, Y.;Zhou, M.-X.; Chen, M.;Su, J.-H.; Du, J.-F.; Song, Q.-L. RSC Adv.2015, 5, 103977. doi: 10.1039/C5RA23950H
29. [29]
  Zhou, Y.;Rao, C.-Q.; Mai, S.-Y.; Song, Q.-L. J. Org. Chem.2016, 81, 2027. doi: 10.1021/acs.joc.5b02887
30. [30]
  Gu, J.;Cai, C. Org. Biomol. Chem.2017, 15, 4226. doi: 10.1039/C7OB00505A
31. [31]
  Ke, J.;Tang, Y.-L.; Yi, H.;Li, Y.-L.; Cheng, Y.-D.; Liu, C.;Lei, A.-W. Angew. Chem., Int. Ed.2015, 54, 6604. doi: 10.1002/anie.201501287
32. [32]
  Liang, W.;Zhang, Z.-J.; Yi, D.;Fu, Q.;Chen, S.-Y.; Yang, L.;Du, F.-T.; Ji, J.-X.; Wei, W. Chin. J. Chem.2017, 35, 1378. doi: 10.1002/cjoc.201700189
33. [33]
  Zhang, Z.-J.; Yi, D.;Fu, Q.;Liang, W.;Chen, S.-Y.; Yang, L.;Du, F.-T.; Ji, J.-X.; Wei, W. Tetrahedron Lett.2017, 58, 2417. doi: 10.1016/j.tetlet.2017.05.005
34. [34]
  Fu, Q.;Yi, D.;Zhang, Z.-J.; Liang, W.;Chen, S.-Y.Yang, L.;Zhang, Q.;Ji, J.-X.; Wei, W. Org. Chem. Front.2017, 4, 1385. doi: 10.1039/C7QO00202E
35. [35]
  Tang, L.;Wen, L.-X.; Sun, T.;Zhang, D.;Yang, Z.;Feng, C.-T.; Wang, Z.-Y. Asian J. Org. Chem.2017, 6, 1683. doi: 10.1002/ajoc.201700434
36. [36]
  Mondal, M.;Bora, U. RSC Adv.2013, 3, 18716. doi: 10.1039/c3ra42480d
37. [37]
  Pan, X.Q.; Zou, J.P.; Zhang, G.L.; Zhang, W. Chem. Commun.2010, 46, 1721. doi: 10.1039/b925951a
38. [38]
  Zhou, J.;Zhang, G.-L.; Zou, J.-P.; Zhang, W. Eur. J. Org. Chem.2011, 3412.
39. [39]
  Zhou, P.;Jiang, Y.-J.; Zou, J.-P.; Zhang, W. Synthesis 2012, 44, 1043. doi: 10.1055/s-0031-1289748
40. [40]
  Zhang, G.-Y.; Li, C.-K.; Li, D.-P.; Zeng, R.-S.; Shoberu, A.;Zou, J.-P. Tetrahedron 2016, 72, 2972. doi: 10.1016/j.tet.2016.04.013
41. [41]
  Zhou, P.;Hu, B.;Li, L.-D.; Rao, K.-R.; Yang, J.;Yu, F.-C. J. Org. Chem.2017, 82, 13268. doi: 10.1021/acs.joc.7b02391
42. [42]
  Tang, P.;Zhang, C.;Chen, E.;Chen, B.;Chen, W.;Yu, Y. Tetrahedron Lett.2017, 58, 2157. doi: 10.1016/j.tetlet.2017.04.069
43. [43]
  Bu, M.-J.; Lu, G.-P.; Cai, C. Catal. Sci. Technol.2016, 6, 413. doi: 10.1039/C5CY01541C
44. [44]
  Liu, D.;Chen, J.-Q.; Wang, X.-Z.; Xu, P.-F. Adv. Synth. Catal.2017, 359, 2773. doi: 10.1002/adsc.201700293
45. [45]
  Qian, H.-F.; Li, C.-K.; Zhou, Z.-H.; Tao, Z.-K.; Shoberu, A.;Zou, J.-P. Org. Lett.2018, 20, 5947. doi: 10.1021/acs.orglett.8b02639
46. [46]
  Shi, Y.;Chen, R.-S.; Guo, K.;Meng, F.;Cao, S.-J.; Gu, C.;Zhu, Y.-G. Tetrahedron Lett.2018, 59, 2062. doi: 10.1016/j.tetlet.2018.04.040
47. [47]
  Peng, P.;Lu, Q.-Q.; Peng, L.;Liu, C.;Wang, G.-Y.; Lei, A.-W. Chem. Commun.2016, 52, 12338. doi: 10.1039/C6CC06881B
48. [48]
  (a) Beller, M.;Seayad, J.;Tillack, A.;Jiao, H. Angew. Chem., Int. Ed.2004, 43, 3368.
  (b) Zeng, X. Chem. Rev.2013, 113, 6864.
49. [49]
  Sturtz, C.C.G.; Normant, H. Bull. Soc. Chim. Fr.1966, 1707.
50. [50]
  Li, X.-B.; Hu, G.-B.; Luo, P.;Tang, G.;Gao, Y.-X.; Xu, P.-X.; Zhao, Y.-F. Adv.Synth.Catal.2012, 354, 2427. doi: 10.1002/adsc.201200420
51. [51]
  Xie, L.-Y.; Yuan, R.;Wang, R.-J.; Peng, Z.-H.; Xiang, J.-N.; He, W.-M. Eur. J. Org. Chem.2014, 13, 2668. doi: 10.1002/chin.201522233
52. [52]
  Xiang, J.-N.; Yi, N.-N.; Wang, R.-J.; Lu, L.-H.; Zou, H.-X.; Pan, Y.;He, W.-M. Tetrahedron 2015, 71, 694. doi: 10.1016/j.tet.2014.12.001
53. [53]
  Liu, K.-J.; Liu, H.-M.; Wang, W.-G.; Ou, L.-J.; Wang, J.-J.Hu, B.-N. Chin. J. Org. Chem.2014, 34, 2007(in Chinese).
54. [54]
  Hou, J.-L.; Chen, Y.;Ma, D.-M.; Cordes, B.;Wang, J.-Y.; Wang, X.;Kühn, F.-E.; Guo, H.;Zhou, M.-D. Chem. Commun.2015, 51, 7439. doi: 10.1039/C5CC01160D
55. [55]
  Zhu, Y.-G. Ph. D. Dissertation, Hunan University, Changsha, 2016(in Chinese).
56. [56]
  Ruan, L.-H.; Wang, Q.;Sun, J.;Zhou, M.-D. Asian J. Org. Chem.2018, 7, 1839. doi: 10.1002/ajoc.201800348
57. [57]
  Chen, L.-L.; Zhang, J.-W.; Yang, W.-W.; Chen, P.;Chen, D.-Y.; Wang, Y.-B. Org. Biomol. Chem.2019, 17, 3003. doi: 10.1039/C9OB00251K
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