Citation: Wang Fangyuan, Yao Keping, Peng Anshun, Wang Chengyu. Progress in the Construction of C-P Bonds[J]. Chemistry, ;2017, 80(6): 524-532, 543. shu

Progress in the Construction of C-P Bonds

School of Chemistry and Chemical Engineering, Linyi University, Linyi 276000

Corresponding author: Wang Chengyu, wangchengyu@lyu.edu.cn
Received Date: 2 August 2016
Accepted Date: 29 December 2016

Figures(1)

Organophosphorus compounds are widely used in pharmacy chemistry, material science, and organic synthesis. So how to construct C-P bonds become a focus in the field of organic synthesis chemistry. In this paper, recent progress in the construction of C-P bonds including traditional synthetic methods, conventional C-P coupling reactions, direct oxidative dehydrogenation coupling, the domino reactions between phosphorus radicals with unsaturated bonds, asymmetric C-P cross-coupling were reviewed. Their advantages and disadvantages, challenges, development directions were also discussed.
- Organophosphorus,
- C-P bonds,
- Coupling reactions,
- Phosphorus radicals
1. [1]
  J L Montchamp. Acc. Chem. Res., 2014, 47(1):77~87.
2. [2]
  S Sivendran, V Jones, D Sun et al. Med. Chem., 2010, 18:896~908.
3. [3]
  (a) Y J Cho, J Y Lee. Chem. Eur. J., 2011, 17(41):11415~11418;(b) S O Jeon, J Y Lee. J. Mater. Chem., 2012, 22:7239~7244;(c) V Bein, S Durganala, A B Morgan. J. Mater. Chem., 2012, 22:1180~1190.
4. [4]
  (a) T Baumgartner, R Reau. Chem. Rev., 2006, 106(11):4681~4727;(b) A R Choudhury, S Mukherjee. Adv. Synth. Catal., 2013, 355(10):1989~1995.
5. [5]
  (a) M N Birkholz, Z Freixa, P W N M van Leeuwen. Chem. Soc. Rev., 2009, 38(4):1099~1118;(b) H Fernández-Pérez, P Etayo, A Panossian et al. Chem. Rev., 2011, 111(3):2119~2176.
6. [6]
  V Mark, J R V Wazer. J. Org. Chem., 1964, 29(5):1006~1008.
7. [7]
  A Michaelis, T Becker. Chem. Ber., 1897, 30:1003~1009.
8. [8]
  F Hossein, M Akbar. Phosphorus Sulfur, 2006, 181:511~518.
9. [9]
  A P Vu, E A Shaffer, C L K Byington et al. Phosphorus Sulfur, 2010, 185(9):1845~1849.
10. [10]
  W Perkow, K Ullerich, F Meyer. Naturwissenschaften, 1952, 39:353~353.
11. [11]
  A M Aguiar, M S Chattha. J. Org. Chem., 1971, 36(18):2719~2720.
12. [12]
  T Hirao, T Masunaga, Y Ohshiro et al. Synthesis, 1981(1), 56~57.
13. [13]
  For copper-catalyzed C-P bond formation, see:(a) T Ogawa, N Usuki, N Ono. J. Chem. Soc., Perkin Transac., 1998, 2953~2958;(b) H H Rao, Y Jin, H Fu et al. Chem. Eur. J., 2006, 12(13):3636~3646;(c) C Huang, X Tang,Y Y Jiang et al. J. Org. Chem., 2006, 71(13):5020~5022.
14. [14]
  T Hirao, T Masunaga, N Yamada et al. Bull. Chem. Soc. Jpn., 1982, 55:909~913
15. [15]
  Y L Zhao, G J Wu, Y Li et al. Chem. Eur. J., 2012, 18(31):9622~9627.
16. [16]
  K Xu, F Yang, G D Zhang et al. Green Chem., 2013, 15:1055~1060.
17. [17]
  K S Petrakis, T L Nagabhushan. J. Am. Chem. Soc., 1987, 109(9):2831~2833.
18. [18]
  C R Shen, G Q Yang, W B Zhang. Org. Biomol. Chem., 2012, 10:3500~3505.
19. [19]
  W C Fu, C M So, F Y Kwong. Org. Lett., 2015, 17(23):5906~5909.
20. [20]
  R Berrino, S Cacchi, G Fabrizi et al. Org. Biomol. Chem., 2010, 8:4518~4520.
21. [21]
  Y He, H M Wu, F D Toste. Chem. Sci., 2015, 6(2):1194~1198.
22. [22]
  J S Zhang, T Q Chen, J Yang et al. Chem. Commun., 2015, 51(35):7540~7542.
23. [23]
  M Andaloussi, J Lindh, J Savmarker et al. Chem. Eur. J., 2009, 15(47):13069~13074.
24. [24]
  R Q Zhuang, J Xu, Z S Cai et al. Org. Lett., 2011, 13(8):2110~2113.
25. [25]
  G B Hu, W Z Chen, T T Fu et al. Org. Lett., 2013, 15(20):5362~5365.
26. [26]
27. [27]
  E R T Tiekink. Crit. Rev. Oncol. Hemat., 2001, 42:217~224.
28. [28]
  H Sun, H Li, P J Sadler. Chem. Ber. Recueil, 1997, 130:669~681.
29. [29]
  T Wang, S Sang, L Liu et al. J. Org. Chem., 2014, 79(2):608~617.
30. [30]
  K Marcin, J Tommy, J Martina et al. Org. Lett., 2010, 12(20):4702~4704.
31. [31]
  J Hu, N Zhao, B Yang et al. Chem. Eur. J., 2011, 17(20):5516~5521.
32. [32]
  Y L Wu, L Liu, K L Yan et al. J. Org. Chem., 2014, 79(17):8118~8127.
33. [33]
  X Li, F Yang, Y J Wu et al. Org. Lett., 2014, 16(3):992~995.
34. [34]
  O Basle, C J Li. Chem. Commun., 2009, (27):4124~4126.
35. [35]
  W Han, A R Ofial. Chem. Commun., 2009, (40):6023~6025.
36. [36]
  M Rueping, S Zhu, R M Koenigs. Chem. Commun., 2011, 47(30):8679~8681.
37. [37]
  W J Yoo, S Kobayashi. Green Chem., 2014, 16:2438~2442.
38. [38]
  J Ke, Y Tang, H Yi et al. Angew. Chem. Int. Ed. 2015, 54(22):6604~6607.
39. [39]
  E F Jason, E K Fields. J. Org. Chem., 1962, 27(4):1402~1405.
40. [40]
  O Tayama, A Nakano, T Iwahama et al. J. Org. Chem., 2004, 69(16):5494~5496.
41. [41]
  X J Mu, J P Zou, Q F Qian et al. Org. Lett., 2006, 8(23):5291~5293.
42. [42]
  C B Xiang, Y J Bian, X R Mao et al. J. Org. Chem., 2012,77(17):7706~7710.
43. [43]
  X Mao, X Ma, S Zhang et al. Eur. J. Org. Chem., 2013, 78(20):4245~4248.
44. [44]
  X L Chen, X Li, L B Qu et al. J. Org. Chem., 2014, 79(17):8407~8416.
45. [45]
  K Luo, Y Z Chen, L X Chen et al. J. Org. Chem., 2016, 81(11):4682~4689.
46. [46]
  C Hou, Y Ren, R Liang et al. Chem. Commun., 2012, 48(42):5181~5183.
47. [47]
  C G Feng, M Te, K J Xiao et al. J. Am. Chem. Soc., 2013, 135(25):9322~9325.
48. [48]
  Y X Gao, G Wang, L Chen et al. J. Am. Chem. Soc., 2009, 131(23):7956~7957.
49. [49]
  T Wang, S T Chen, A L Shao et al. Org. Lett., 2015, 17(1):118~121.
50. [50]
  A R Stiles, W E Vaughan, F F Rust. J. Am. Chem. Soc., 1958, 80(3):714~716.
51. [51]
  X Q Pan, L Wang, J P Zou et al. Chem. Commun. 2011, 47(27):7875~7877.
52. [52]
  L J Wang, A Q Wang, Y Xia et al. Chem. Commun. 2014, 50(90):13998~4001.
53. [53]
  H L Hua, B S Zhang, Y T He et al. Org. Lett., 2016, 18(2):216~219.
54. [54]
  Y Z Gao, X Q Li, J Xu et al. Chem. Commun., 2015, 51(9):1605~1607.
55. [55]
  Y Z Gao, G Z Lu, P B Zhang et al. Org. Lett., 2016, 18(6):1242~1245.
56. [56]
  W Wei, J X Ji. Angew. Chem. Int. Ed., 2011, 50(39):9097~9099.
57. [57]
  N N Yi, R J Wang, H X Zou et al. J. Org. Chem., 2015, 80(10):5023~5029.
58. [58]
  C W Zhang, Z D Li, L Zhu et al. J. Am. Chem. Soc., 2013, 135(38):14082~14085.
59. [59]
  Z Z Zhou, D P Jin, L H Li et al. Org. Lett., 2014, 16(21):5616~5619.
60. [60]
  Q W Gui, L Hu, X Chen et al. Chem. Commun., 2015, 51(73):13922~13924.
61. [61]
  S F Zhou, D P Li, K Liu et al. J. Org. Chem., 2015, 80(2):1214~1220.
62. [62]
  T Yokomatss,T Yamagisbi, S Shibuya. Tetrahed.:Asymm., 1993, 4(8):1779~1782.
63. [63]
  M D Groaning, B J Rowe, C D Spilling. Tetrahed. Lett., 1998, 39(31):5485~5488.
64. [64]
  I Schlemminger, Y Saida, H Gr ger et al. J. Org. Chem., 2000, 65(16):4818~4825.
65. [65]
  (a) S H Gou, X Zhou, J Wang et al. Tetrahedron, 2008, 64(12):2864~2870;(b) B Saito, H Egami, T Katsuki. J. Am. Chem. Soc., 2007, 129(7):1978~1986;(c) B Saito, T Katsuki. Angew. Chem. Int. Ed., 2005, 44(29):4600~4602.
66. [66]
  W L Chen, Y H Hui, X Zhou et al. Tetrahed. Lett., 2010, 51(32):4175~4178.
67. [67]
  (a) H Sasai, S Arai, Y Tahara. J. Org. Chem., 1995, 60(21):6656~6657.(b) H Sasai, M Bougauchi, T Arai et al. Tetrahed. Lett., 1997, 38(15):2717~2720.
68. [68]
  T Arai, M Bougauchi, H Sasai et al. J. Org. Chem., 1996, 61(9):2926~2927.
69. [69]
  K Bravo-Altamirano, L Coudray, E L Deal et al. Org. Biomol. Chem., 2010, 8:5541~5551.
70. [70]
  C Scriban, D S Glueck. J. Am. Chem. Soc., 2006, 128(9):2788~2789.
71. [71]
  J R Moncarz, N F Laritcheva, D S Glueck. J. Am. Chem. Soc., 2002, 124(45):13356~13357.
72. [72]
  B J Anderson, M A Guino-o, D S Glueck et al. Org. Lett., 2008, 10(20):4425~4428.
73. [73]
  V Bhat, S Wang, B M Stoltz et al. J. Am. Chem. Soc., 2013, 135(45):16829~16832.
74. [74]
  P Ramírez-López, A Ros, B Estepa et al. ACS Catal., 2016, 6(6):3955~3964.
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