Synthesis of 6-(arylthio)phenanthridines by copper-catalyzed tandem reactions of 2-biaryl isothiocyanates with diaryliodonium salts

Organic Letters

Volumn 17, Issue 5, 2015, Pages 1232-1235

  Guo, Weisi ^a   Li, Shoulei ^a   Tang, Lin ^a   Li, Ming ^a   Wen, Lirong ^a   Chen, Chao ^b  

^a QINGDAO UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b TSINGHUA UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; CATION; COPPER; INORGANIC SALT; ISOTHIOCYANIC ACID; ISOTHIOCYANIC ACID DERIVATIVE; PHENANTHRIDINE DERIVATIVE; TRISPHERIDINE;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

CATALYSIS; COPPER; DIOXOLES; ISOTHIOCYANATES; MOLECULAR STRUCTURE; ONIUM COMPOUNDS; PHENANTHRIDINES; SALTS;

EID: 84924254626     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b00197     Document Type: Article

References (73)

1. Suffnes, M.; Cordell, G. A. The Alkaloids; Academic: New York, 1985; Vol. 25, pp 178-189.
2. Nakanishi, T.; Suzuki, M.; Saimoto, A.; Kabasawa, T. J. Nat. Prod. 1999, 62, 864-867
3. Ishikawa, T. Med. Res. Rev. 2001, 21, 61-72
4. Hu, J.; Shi, X.; Chen, J.; Mao, X.; Zhu, L.; Yu, L.; Shi, J. Food Chem. 2014, 148, 437-444
5. Dubost, E.; Dumas, N.; Fossey, C.; Magnelli, R.; Butt-Gueulle, S.; Ballandonne, C.; Caignard, D. H.; Dulin, F.; Sopkova de-Oliveira Santos, J.; Millet, P.; Charnay, Y.; Rault, S.; Cailly, T.; Fabis, F. J. Med. Chem. 2012, 55, 9693-9707
6. Nagesh, H. N.; Naidu, K. M.; Rao, D. H.; Sridevi, J. P.; Sriram, D.; Yogeeswari, P.; Chandra Sekhar, K. V. Bioorg. Med. Chem. Lett. 2013, 23, 6805-6810
7. Chen, H.; Long, H.; Cui, X.; Zhou, J.; Xu, M.; Yuan, G. J. Am. Chem. Soc. 2014, 136, 2583-2591
8. Cheng, P.; Zhou, J.; Qing, Z.; Kang, W.; Liu, S.; Liu, W.; Xie, H.; Zeng, J. Bioorg. Med. Chem. Lett. 2014, 24, 2712-2716
9. Nguyen, P.; Oumata, N.; Soubigou, F.; Evrard, J.; Desban, N.; Lemoine, P.; Bouaziz, S.; Blondel, M.; Voisset, C. Eur. J. Med. Chem. 2014, 82, 363-371
10. Park, G. Y.; Wilson, J. J.; Song, Y.; Lippard, S. J. Proc. Natl. Acad. Sci. U.S.A. 2012, 109, 11987-11992
11. Johnstone, T. C.; Alexander, S. M.; Lin, W.; Lippard, S. J. J. Am. Chem. Soc. 2014, 136, 116-118
12. Zhang, J.; Lakowicz, J. R. J. Phys. Chem. B 2005, 109, 8701-8706
13. Stevens, N.; O'Connor, N.; Vishwasrao, H.; Samaroo, D.; Kandel, E. R.; Akins, D. L.; Drain, C. M.; Turro, N. J. J. Am. Chem. Soc. 2008, 130, 7182-7183
14. Gerfaud, T.; Neuville, L.; Zhu, J. Angew. Chem., Int. Ed. 2009, 48, 572-577
15. Maestri, G.; Larraufie, M. H.; Derat, E.; Ollivier, C.; Fensterbank, L.; Lacote, E.; Malacria, M. Org. Lett. 2010, 12, 5692-5695
16. McBurney, R. T.; Slawin, A. M.; Smart, L. A.; Yu, Y.; Walton, J. C. Chem. Commun. 2011, 47, 7974-7976
17. Wu, Y.; Wong, S. M.; Mao, F.; Chan, T. L.; Kwong, F. Y. Org. Lett. 2012, 14, 5306-5309
18. Wang, W. Y.; Feng, X.; Hu, B. L.; Deng, C. L.; Zhang, X. G. J. Org. Chem. 2013, 78, 6025-6030
19. Chen, Y. F.; Hsieh, J. C. Org. Lett. 2014, 16, 4642-4645
20. Li, J.; Wang, H.; Sun, J.; Yang, Y.; Liu, L. Org. Biomol. Chem. 2014, 12, 7904-7908
21. Tummatorn, J.; Krajangsri, S.; Norseeda, K.; Thongsornkleeb, C.; Ruchirawat, S. Org. Biomol. Chem. 2014, 12, 5077-5081
22. Tobisu, M.; Koh, K.; Furukawa, T.; Chatani, N. Angew. Chem., Int. Ed. 2012, 51, 11363-11366
23. Zhang, B.; Muck-Lichtenfeld, C.; Daniliuc, C. G.; Studer, A. Angew. Chem., Int. Ed. 2013, 52, 10792-10795
24. Jiang, H.; Cheng, Y.; Wang, R.; Zheng, M.; Zhang, Y.; Yu, S. Angew. Chem., Int. Ed. 2013, 52, 13289-13292
25. Wang, Q.; Dong, X.; Xiao, T.; Zhou, L. Org. Lett. 2013, 15, 4846-4849
26. Cheng, Y.; Jiang, H.; Zhang, Y.; Yu, S. Org. Lett. 2013, 15, 5520-5523
27. Leifert, D.; Daniliuc, C. G.; Studer, A. Org. Lett. 2013, 15, 6286-6289
28. Zhang, B.; Daniliuc, C. G.; Studer, A. Org. Lett. 2014, 16, 250-253
29. Xia, Z.; Huang, J.; He, Y.; Zhao, J.; Lei, J.; Zhu, Q. Org. Lett. 2014, 16, 2546-2549
30. Gu, L.; Jin, C.; Liu, J.; Ding, H.; Fan, B. Chem. Commun. 2014, 50, 4643-4645
31. Cao, J. J.; Zhu, T. H.; Wang, S. Y.; Gu, Z. Y.; Wang, X.; Ji, S. J. Chem. Commun. 2014, 50, 6439-6442
32. Li, Z.; Fan, F.; Yang, J.; Liu, Z. Q. Org. Lett. 2014, 16, 3396-3399
33. Pan, C.; Han, J.; Zhang, H.; Zhu, C. J. Org. Chem. 2014, 79, 5374-5378
34. Fang, H.; Zhao, J.; Qian, P.; Han, J.; Pan, Y. Asian J. Org. Chem. 2014, 3, 1266-1269
35. Ilardi, E. A.; Vitaku, E.; Njardarson, J. T. J. Med. Chem. 2014, 57, 2832-2842
36. Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2002, 4, 3517-3520
37. Fernández-Rodríguez, M. A.; Shen, Q.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 2180-2181
38. Hartwig, J. F. Acc. Chem. Res. 2008, 41, 1534-1544
39. Chu, L.; Yue, X.; Qing, F. L. Org. Lett. 2010, 12, 1644-1647
40. Zou, L. H.; Reball, J.; Mottweiler, J.; Bolm, C. Chem. Commun. 2012, 48, 11307-11309
41. Chen, F. J.; Liao, G.; Li, X.; Wu, J.; Shi, B. F. Org. Lett. 2014, 16, 5644-5647
42. Wang, P. F.; Wang, X. Q.; Dai, J. J.; Feng, Y. S.; Xu, H. J. Org. Lett. 2014, 16, 4586-4589
43. Tang, R. Y.; Xie, Y. X.; Xie, Y. L.; Xiang, J. N.; Li, J. H. Chem. Commun. 2011, 47, 12867-12869
44. Badsara, S. S.; Liu, Y. C.; Hsieh, P. A.; Zeng, J. W.; Lu, S. Y.; Liu, Y. W.; Lee, C. F. Chem. Commun. 2014, 50, 11374-11377
45. Du, B.; Jin, B.; Sun, P. Org. Lett. 2014, 16, 3032-3035
46. Luo, Y.; Pan, X.; Chen, C.; Yao, L.; Wu, J. Chem. Commun. 2015, 51, 180-182
47. Kondo, T.; Mitsudo, T. Chem. Rev. 2000, 100, 3205-3220
48. Beletskaya, I. P.; Ananikov, V. P. Chem. Rev. 2011, 111, 1596-1636
49. Lee, C. F.; Liu, Y. C.; Badsara, S. S. Chem.-Asian. J. 2014, 9, 706-722
50. Goldberg, A. F.; O'Connor, N. R.; Craig, R. A., II; Stoltz, B. M. Org. Lett. 2012, 14, 5314-5317
51. Zhao, P.; Yan, X.; Yin, H.; Xi, C. Org. Lett. 2014, 16, 1120-1123
52. Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584
53. Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299-5358
54. Merritt, E. A.; Olofsson, B. Angew. Chem., Int. Ed. 2009, 48, 9052-9070
55. Phipps, R. J.; McMurray, L.; Ritter, S.; Duong, H. A.; Gaunt, M. J. J. Am. Chem. Soc. 2012, 134, 10773-10776
56. Ghosh, R.; Stridfeldt, E.; Olofsson, B. Chem.-Eur. J. 2014, 20, 8888-8892
57. Jiang, H.; Cheng, Y.; Wang, R.; Zhang, Y.; Yu, S. Chem. Commun. 2014, 50, 6164-6167
58. Li, P.; Cheng, G.; Zhang, H.; Xu, X.; Gao, J.; Cui, X. J. Org. Chem. 2014, 79, 8156-8162
59. Zhang, F.; Das, S.; Walkinshaw, A. J.; Casitas, A.; Taylor, M.; Suero, M. G.; Gaunt, M. J. J. Am. Chem. Soc. 2014, 136, 8851-8854
60. Zhou, B.; Hou, W.; Yang, Y.; Feng, H.; Li, Y. Org. Lett. 2014, 16, 1322-1325
61. Bunnett, J. F.; Zahler, R. E. Chem. Rev. 1951, 49, 273-412
62. Wang, L.; Chen, Z. C. Syn. Commun. 2001, 31, 1227-1232
63. Papadopoulou, M.; Spyroudis, S.; Varvoglis, A. J. Org. Chem. 1985, 50, 1509-1511
64. Wagner, A. M.; Sanford, M. S. J. Org. Chem. 2014, 79, 2263-2267
65. Spyroudis, S. P. Liebigs Ann. Chem. 1986, 947-951
66. Wang, Y.; Chen, C.; Peng, J.; Li, M. Angew. Chem., Int. Ed. 2013, 52, 5323-5327
67. Pang, X.; Chen, C.; Su, X.; Li, M.; Wen, L. Org. Lett. 2014, 16, 6228-6231
68. Wang, Y.; Li, M.; Wen, L.; Jing, P.; Su, X.; Chen, C. Org. Biomol. Chem. 2015, 13, 751-763
69. Xu, J.; Zhang, P.; Gao, Y.; Chen, Y.; Tang, G.; Zhao, Y. J. Org. Chem. 2013, 78, 8176-8183
70. Tanner, D. D.; Reed, D. W.; Setiloane, B. P. J. Am. Chem. Soc. 1982, 104, 3917-3923
71. Crivello, J. V.; Lam, J. H. W. J. Org. Chem. 1978, 43, 3055-3058
72. Krief, A.; Dumont, W.; Robert, M. Synlett 2006, 484-486
73. Viladomat, F.; Selles, M.; Codina, C.; Bastida, J. Planta Med. 1997, 63, 583