Silver-mediated oxidative C-H/P-H functionalization: An efficient route for the synthesis of benzo[b]phosphole oxides

Journal of the American Chemical Society

Volumn 135, Issue 45, 2013, Pages 16754-16757

  Chen, Yun Rong ^a   Duan, Wei Liang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLPHOSPHINE; BOND CLEAVAGES; BOND FORMATION; DIRECT PREPARATION; FUNCTIONALIZATION REACTIONS; FUNCTIONALIZATIONS; INTERNAL ALKYNES; RADICAL PROCESS;

CHEMISTRY; SYNTHESIS (CHEMICAL);

SILVER;

ALKYNE DERIVATIVE; OXIDE; PHOSPHINE DERIVATIVE; SILVER;

ARTICLE; ATOM; CHEMICAL BOND; CYCLIZATION; MIGRATION; OXIDATION; QUANTUM YIELD; SYNTHESIS;

BENZENE DERIVATIVES; OXIDATION-REDUCTION; OXIDES; PHOSPHINES; SILVER;

EID: 84887708271     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja407373g     Document Type: Article

References (71)

1. Phosphorus Heterocycles II; Bansal, R. K., Ed.; Topics in Heterocyclic Chemistry; Springer, Berlin, 2010; Vol. 21.
2. Phosphorus Ligands in Asymmetric Catalysis: Synthesis and Applications; Börner, A., Ed.; Wiley-VCH: Weinheim, 2008; Vols. 1-3.
3. Phosphorus Compounds: Advanced Tools in Catalysis and Material Sciences; Peruzzini, M., Gonsalvi, L., Ed.; Springer: Berlin, 2011.
4. Matano, Y.; Imahori, H. Org. Biomol. Chem. 2009, 7, 1258
5. Mathey, F. Acc. Chem. Res. 2004, 37, 954
6. Tsuji, H.; Sato, K.; IIies, L.; Itoh, Y.; Sato, Y.; Nakamura, E. Org. Lett. 2008, 10, 2263
7. Sanji, T.; Shiraishi, K.; Kashiwabara, T.; Tanaka, M. Org. Lett. 2008, 10, 2689
8. Fukazawa, A.; Ichihashi, Y.; Kosaka, Y.; Yamaguchi, S. Chem.-Asian J. 2009, 4, 1729
9. Hayashi, Y.; Matano, Y.; Suda, K.; Kimura, Y.; Nakao, Y.; Imahori, H. Chem.-Eur. J. 2012, 18, 15972
10. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094
11. Gutekunst, W. R.; Baran, P. S. Chem. Soc. Rev. 2011, 40, 1976
12. Stokes, B. J.; Briver, T. G. Eur. J. Org. Chem. 2011, 4071
13. Mei, T.-S.; Kou, L.; Ma, S.; Engle, K. M.; Yu, J.-Q. Synthesis 2012, 44, 1778
14. Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed. 2012, 51, 8960
15. Wencel-Delord, J.; Glorius, F. Nat. Chem. 2012, 5, 369
16. Yoshikai, N.; Wei, Y. Asian J. Org. Chem. 2013, 2, 466
17. Würtz, S.; Rakshit, S.; Neumann, J. J.; Dröge, T.; Glorius, F. Angew. Chem., Int. Ed. 2008, 47, 7230
18. Stuart, D. R.; Bertrand-Laperle, M.; Burgess, K. M. N.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 16474
19. Shi, Z.; Zhang, C.; Li, S.; Pan, D.; Ding, S.; Cui, Y.; Jiao, N. Angew. Chem., Int. Ed. 2009, 48, 4572
20. Bernini, R.; Fabrizi, G.; Sferrazza, A.; Cacchi, S. Angew. Chem., Int. Ed. 2009, 48, 8078
21. Yu, W.; Du, Y.; Zhao, K. Org. Lett. 2009, 11, 2417
22. Stuart, D. R.; Alsabeh, P.; Kuhn, M.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 18326
23. Chen, J.; Song, G.; Pan, C.-L.; Li, X. Org. Lett. 2010, 12, 5426
24. Guan, Z.-H.; Yan, Z.-Y.; Ren, Z.-H.; Liu, X.-Y.; Liang, Y.-M. Chem. Commun. 2010, 46, 2823
25. Huestis, M. P.; Chan, L.; Stuart, D. R.; Fagnou, K. Angew. Chem., Int. Ed. 2011, 50, 1338
26. Wei, Y.; Deb, I.; Yoshikai, N. J. Am. Chem. Soc. 2012, 134, 9098
27. Shi, Z.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 9220
28. Rakshit, S.; Patureau, F. W.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 9585
29. Zhao, M.; Wang, F.; Li, X. Org. Lett. 2012, 14, 1412
30. Wang, L.; Ackermann, L. Org. Lett. 2013, 15, 176
31. Shi, Z.; Suri, M.; Glorius, F. Angew. Chem., Int. Ed. 2013, 52, 4892
32. Wasa, M.; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 14058
33. Lu, Y.; Wang, D.-H.; Engle, K. M.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 5916
34. Guimond, N.; Gouliaras, C.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 6908
35. Su, Y.; Zhao, M.; Han, K.; Song, G.; Li, X. Org. Lett. 2010, 12, 5462
36. Song, G.; Chen, D.; Pan, C.-L.; Crabtree, R. H.; Li, X. J. Org. Chem. 2010, 75, 7487
37. Lu, Y.; Leow, D.; Wang, X.; Engle, K. M.; Yu, J.-Q. Chem. Sci. 2011, 2, 967
38. Ackermann, L.; Lygin, A. V.; Hofmann, N. Angew. Chem., Int. Ed. 2011, 50, 6379
39. Guimond, N.; Gorelsky, S. I.; Fagnou, K. J. Am. Chem. Soc. 2011, 133, 6449
40. Ma, W.; Graczyk, K.; Ackermann, L. Org. Lett. 2012, 14, 6318
41. Deponti, M.; Kozhushkov, S. I.; Yufit, D. S.; Ackermann, L. Org. Biomol. Chem. 2013, 11, 142
42. Cheng, X.-F.; Li, Y.; Su, Y.-M.; Yin, F.; Wang, J.-Y.; Sheng, J.; Vora, H. U.; Wang, X.-S.; Yu, J.-Q. J. Am. Chem. Soc. 2013, 135, 1236
43. Kuninobu, Y.; Yoshida, T.; Takai, K. J. Org. Chem. 2011, 76, 7370
44. Hou, C.; Ren, Y.; Lang, R.; Hu, X.; Xia, C.; Li, F. Chem. Commun. 2012, 48, 5181
45. Wang, C.-B.; Bian, Y.-J.; Mao, X.-R.; Huang, Z.-Z. J. Org. Chem. 2012, 77, 7706
46. Wang, H.; Li, X.; Wu, F.; Wan, B. Synthesis 2012, 44, 941
47. Sun, M.; Wang, H.-L.; Ting, Q.-P.; Yang, S.-D. Angew. Chem., Int. Ed. 2013, 52, 3972
48. Feng, C.-G.; Ye, M.; Xiao, K.-J.; Li, S.; Yu, J.-Q. J. Am. Chem. Soc. 2013, 135, 9322
49. Albrecht, M. Chem. Rev. 2010, 110, 576
50. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624
51. Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651
52. Dubrovina, N. V.; Börner, A. Angew. Chem., Int. Ed. 2004, 43, 5883
53. Shaikh, T. M.; Weng, C.-M.; Hong, F.-E. Coord. Chem. Rev. 2012, 256, 771
54. He, C.; Guo, S.; Ke, J.; Hao, J.; Xu, H.; Chen, H.; Lei, A. J. Am. Chem. Soc. 2012, 134, 5766
55. He, C.; Hao, J.; Xu, H.; Mo, Y.; Liu, H.; Han, J.; Lei, A. Chem. Commun. 2012, 48, 11073
56. Studer, A.; Bossart, M. Tetrahedron 2001, 57, 9649
57. Bowman, W. R.; Storey, J. M. D. Chem. Soc. Rev. 2007, 36, 1803
58. Clive, D. L. J.; Kang, S. Tetrahedron Lett. 2000, 41, 1315
59. Clive, D. L. J.; Kang, S. J. Org. Chem. 2001, 66, 6083
60. For a review on the interpretation of deuterium kinetic isotope effects in C-H bond functionalization, see: Simmons, E. M.; Hartwig, J. F. Angew. Chem., Int. Ed. 2012, 51, 3066
61. Hunt, B. B.; Saunders, B. C. J. Chem. Soc. 1957, 2413
62. Ye, Y. D.; Lee, S. H.; Sanford, M. S. Org. Lett. 2011, 13, 5464
63. Maity, S.; Manna, S.; Rana, S.; Naveen, T.; Mallick, A.; Maiti, D. J. Am. Chem. Soc. 2013, 135, 3355
64. Demir, A. S.; Emrullahoglu, M. Curr. Org. Synth. 2007, 4, 321
65. Tayama, O.; Nakano, A.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2004, 69, 5494
66. Kagayama, T.; Nakano, A.; Sakaguchi, S.; Ishii, Y. Org. Lett. 2006, 8, 407
67. Mu, X.-J.; Zou, J.-P.; Qian, Q.-F.; Zhang, W. Org. Lett. 2006, 8, 5291
68. Pan, X.-Q.; Zou, J.-P.; Zhang, G.-L.; Zhang, W. Chem. Commun. 2010, 46, 1721
69. Zhou, J.; Zhang, Z.-G.; Zou, J.-P.; Zhang, W. Eur. J. Org. Chem. 2011, 3412
70. Pan, X.-Q.; Wang, L.; Zou, J.-P.; Zhang, W. Chem. Commun. 2011, 47, 7875
71. Wang, G.-W.; Wang, C.-Z.; Zou, J.-P. J. Org. Chem. 2011, 76, 6088