6-phosphorylated phenanthridines from 2-isocyanobiphenyls via radical C-P and C-C bond formation

Organic Letters

Volumn 16, Issue 1, 2014, Pages 250-253

  Zhang, Bo ^a   Daniliuc, Constantin Gabriel ^a   Studer, Armido ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BIPHENYL DERIVATIVE; FREE RADICAL; NITRILE; PHENANTHRIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; PHOSPHORYLATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

BIPHENYL COMPOUNDS; CRYSTALLOGRAPHY, X-RAY; FREE RADICALS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NITRILES; PHENANTHRIDINES; PHOSPHORYLATION;

EID: 84891800073     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol403256e     Document Type: Article

References (72)

1. Organic Phosphorus Compounds; Kosolapoff, G. M., Maier, L., Eds.; Wiley-Interscience: New York, 1972.
2. Corbridge, D. E. C. Phosphorus: Chemistry, Biochemistry and Technology, 6th ed.; CRC Press: London, 2013.
3. Kolio, D. T. Chemistry and Application of H-Phosphonates; Elsevier Science: Oxford, 2006.
4. Quin, L. D. A Guide to Organophosphorus Chemistry; Wiley-Interscience: Hoboken, NJ, 2000.
5. Bhattacharta, A. K.; Thyagarajan, G. Chem. Rev. 1981, 81, 415
6. Giorgio, C.; Gianmauro, O.; Gerard, A. P. Tetrahedron 2003, 59, 9471
7. Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029
8. Sivendran, S.; Jones, V.; Sun, D.; Wang, Y.; Grzegorzewicz, A. E.; Scherman, M. S.; Napper, A. D.; McCammon, J. A.; Lee, R. E.; Diamond, S. L.; McNeil, M. Bioorg. Med. Chem. 2010, 18, 896
9. Dang, Q.; Liu, Y.; Cashion, D. K; Kasib-hatla, S. R.; Jiang, T.; Taplin, F.; Jacintho, J. D.; Li, H.; Sun, Z.; Fan, Y.; DaRe, J.; Tian, F.; Li, W.; Gibson, T.; Lemus, R.; van Poelje, P. D.; Potter, S. C.; Erion, M. D. J. Med. Chem. 2011, 54, 153
10. Chen, X.; Kopecky, D. J.; Mihalic, J.; Jeffries, S.; Min, X.; Heath, J.; Deignan, J.; Lai, S.; Fu, Z.; Guimaraes, C.; Shen, S.; Li, S.; Johnstone, S.; Thibault, S.; Xu, H.; Cardozo, M.; Shen, W.; Walker, N.; Kayser, F.; Wang, Z. J. Med. Chem. 2012, 55, 3837
11. Steininger, H.; Schuster, M.; Kreuer, K. D.; Kaltbeitzel, A.; Bingol, B.; Meyer, W. H.; Schauff, S.; Brunklaus, G.; Maier, J.; Spiess, H. W. Phys. Chem. Chem. Phys. 2007, 9, 1764
12. Kirumakki, S.; Huang, J.; Subbiah, A.; Yao, J.; Rowland, A.; Smith, B.; Mukherjee, A.; Samarajeewa, S.; Clearfield, A. J. Mater. Chem. 2009, 19, 2593
13. Spampinato, V.; Tuccitto, N.; Quici, S.; Calabrese, V.; Marletta, G.; Torrisi, A.; Licciardello, A. Langmuir 2010, 26, 8400
14. Li, X. S.; Zhang, D. W.; Pang, H.; Shen, F.; Fu, H.; Jiang, Y. Y.; Zhao, Y. F. Org. Lett. 2005, 7, 4919
15. Yu, X.; Ding, Q.; Wu, J. J. Comb. Chem. 2010, 12, 743
16. Schwan, A. L. Chem. Soc. Rev. 2004, 33, 218
17. Jeught, S. V. D.; Stevens, C. V. Chem. Rev. 2009, 109, 2672
18. Glueck, D. S. Top. Organomet. Chem. 2010, 31, 65
19. Tappe, F. M. J.; Trepohl, V. T.; Oestreich, M. Top. Synthesis 2010, 3037
20. Montchamp, J.-L. Acc. Chem. Res. 2013, 10.1021/ar400071v
21. Hirao, T.; Masunaga, T.; Ohshiro, Y.; Agawa, T. Synthesis 1981, 56
22. Gelman, D.; Jiang, L.; Buchwald, S. L. Org. Lett. 2003, 5, 2315
23. Kalek, M.; Ziadi, A.; Stawinski, J. Org. Lett. 2008, 10, 4637
24. Deal, E. L.; Petit, C.; Montchamp, J.-L. Org. Lett. 2011, 13, 3270
25. Zhang, X. H.; Liu, H. Z.; Hu, X. M.; Tang, G.; Zhu, J.; Zhao, Y. Org. Lett. 2011, 13, 3478
26. Rummelt, S. M.; Ranocchiari, M.; Bokhoven, J. A. Org. Lett. 2012, 14, 2188
27. Xu, K.; Yang, F.; Zhang, G.; Wu, Y. Green. Chem. 2013, 15, 1055
28. Zhao, Y.-L.; Wu, G.-J.; Li, Y.; Gao, L.-X.; Han, F.-S. Chem.-Eur. J. 2012, 18, 9622
29. For radical phosphanylation of aryl halides, see Vaillard, S. E.; Mück-Lichtenfeld, C.; Grimme, S.; Studer, A. Angew. Chem., Int. Ed. 2007, 46, 6533
30. Bruch, A.; Ambrosius, A.; Fröhlich, R.; Studer, A.; Guthrie, D. B.; Zhang, H.; Curran, D. P. J. Am. Chem. Soc. 2010, 132, 11452
31. Bruch, A.; Fukazawa, A.; Yamaguchi, E.; Yamaguchi, S.; Studer, A. Angew. Chem., Int. Ed. 2011, 50, 12094
32. Petrakis, K. S.; Nagabhushan, T. L. J. Am. Chem. Soc. 1987, 109, 2831
33. Luo, Y.; Wu, J. Organometallics 2009, 28, 6823
34. Berrino, R.; Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Stabile, P. Org. Biomol. Chem. 2010, 8, 4518
35. Andaloussi, M.; Lindh, J.; Sävmarker, J.; Sjöberg, P. J. R.; Larhed, M. Chem.-Eur. J. 2009, 15, 13069
36. Hu, G.; Chen, W.; Fu, T.; Peng, Z.; Qiao, H.; Cao, Y.; Zhao, Y. Org. Lett. 2013, 15, 5362
37. Zhuang, R.; Xu, J.; Cai, Z.; Tang, G.; Fang, M.; Zhao, Y. Org. Lett. 2011, 13, 2110
38. Li, C.; Yano, T.; Ishida, N.; Murakami, M. Angew. Chen., Int. Ed. 2013, 52, 9801
39. Feng, C.-G.; Ye, M.; Xiao, K.-J.; Li, S.; Yu, J.-Q. J. Am. Chem. Soc. 2013, 135, 9322
40. Hou, C.; Re, Y.; Lang, R.; Hu, X.; Xia, C.; Li, F. Chem. Commun. 2012, 48, 5181
41. Kuninobu, Y.; Yoshida, T.; Takai, K. J. Org. Chem. 2011, 76, 7370
42. Mao, X.; Ma, X.; Zhang, S.; Hu, H.; Zhu, C.; Cheng, Y. Eur. J. Org. Chem. 2013, 4245
43. Xiang, C.-B.; Bian, Y.-J.; Mao, X.-R.; Huang, Z.-Z. J. Org. Chem. 2012, 77, 7706
44. Kagayama, T.; Nakano, A.; Sakaguchi, S.; Ishii, Y. Org. Lett. 2006, 8, 407
45. Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1992, 114, 5863
46. Curran, D. P.; Ko, S.-B.; Josien, H. Angew. Chem., Int. Ed. 1996, 34, 2683
47. Nanni, D.; Pareschi, P.; Rizzoli, C.; Sgarabotto, P.; Tundo, T. Tetrahedron 1995, 51, 9045
48. Yamago, S.; Miyazoe, H.; Coto, R.; Hashidume, M.; Sawazaki, T.; Yoshida, I. J. Am. Chem. Soc. 2001, 123, 3697
49. Janza, B.; Studer, A. Org. Lett. 2006, 8, 1875
50. Tobisu, M.; Koh, K.; Furukawa, T.; Chatani, N. Angew. Chem., Int. Ed. 2012, 51, 11363
51. Mitamura, T.; Iwata, K.; Ogawa, A. J. Org. Chem. 2011, 76, 3880
52. Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177
53. Spagnolo, D.; Nanni, D. In Encyclopedia of Radicals in Chemistry, Biology and Materials; Chatgilialoglu, C.; Studer, A., Eds.; John Wiley & Sons: Chichester, 2012; Vol. 2, p 1019.
54. Zhang, B.; Mück-Lichtenfeld, C.; Daniliuc, C. G.; Studer, A. Angew. Chem., Int. Ed. 2013, 52, 10792
55. Wang, Q.; Dong, X.; Xiao, T.; Zhou, L. Org. Lett. 2013, 15, 4846
56. Leifert, D.; Daniliuc, C. G.; Studer, A. Org. Lett. 2013, 10.1021/ol403147v
57. Zhou, J.; Zhang, G.-L.; Zou, J.-P.; Zhang, W. Eur. J. Org. Chem. 2011, 3412
58. Pan, X.-Q.; Zou, J.-P.; Zhang, G.-L.; Zhang, W. Chem. Commun. 2010, 46, 1721
59. Pan, X.-Q.; Wang, Lu.; Zou, J.-P.; Zhang, W. Chem. Commun. 2011, 47, 7875
60. Tayama, O.; Nakano, A.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2004, 69, 5494
61. Snider, B. B. Chem. Rev. 1996, 96, 339
62. Zhang, C.; Li, Z.; Zhu, L.; Yu, L.; Wang, Z.; Li, C. J. Am. Chem. Soc. 2013, 135, 14082
63. Unoh, Y.; Hirano, K.; Satoh, T.; Miura, M. Angew. Chen. Int. Ed. 2013, 52, 12975
64. Wang, H.; Li, X.; Wu, F.; Wan, B. Synthesis 2012, 941
65. Review: Finkbeiner, P.; Nachtsheim, B. J. Synthesis 2013, 979
66. See also: Wertz, S.; Leifert, D.; Studer, A. Org. Lett. 2013, 15, 928
67. Leca, D.; Fensterbank, L.; Lacote, E.; Malacria, M. Chem. Soc. Rev. 2005, 34, 858
68. Baralle, A.; Baroudi, A.; Daniel, M.; Fensterbank, L.; Goddard, J.-P.; Lacote, E.; Larraufie, M.-H.; Maestri, G.; Malacria, M.; Ollivier, C. In Encyclopedia of Radicals in Chemistry, Biology and Materials; Chatgilialoglu, C.; Studer, A., Eds.; John Wiley & Sons: Chichester, 2012; Vol. 2, p 767.
69. Simeon, S.; Rios, J. L.; Villar, A. Pharmazie 1989, 44, 593
70. Phillips, S. D.; Castle, R. N. J. Heterocycl. Chem. 1981, 18, 223
71. Abdel-Halim, O. B.; Morikawa, T.; Ando, S.; Matsuda, H.; Yoshikawa, M. J. Nat. Prod. 2004, 67, 1119
72. Sripada, L.; Teske, J. A.; Deiters, A. Org. Biomol. Chem. 2008, 6, 263