Palladium-catalyzed oxidative insertion of carbon monoxide to N -sulfonyl-2-aminobiaryls through C-H bond activation: Access to bioactive phenanthridinone derivatives in one pot

Organic Letters

Volumn 15, Issue 7, 2013, Pages 1468-1471

  Rajeshkumar, Venkatachalam ^a   Lee, Tai Hua ^a   Chuang, Shih Ching ^a  

^a NATIONAL CHIAO TUNG UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

AMARYLLIDACEAE ALKALOID; CARBON MONOXIDE; PALLADIUM; PHENANTHRENE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; OXIDATION REDUCTION REACTION; SYNTHESIS;

AMARYLLIDACEAE ALKALOIDS; CARBON MONOXIDE; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PALLADIUM; PHENANTHRENES;

EID: 84875952816     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol4001922     Document Type: Article

References (64)

1. Ghosal, S.; Lochan, R.; Ashutosh, K.; Yatendra, S.; Radhey, S. Phytochemistry 1985, 24, 1825-1828
2. Ghosal, S.; Rao, P. H.; Jaiswal, D. K.; Kumar, Y.; Frahm, A. W. Phytochemistry 1981, 20, 2003-2007
3. Harayama, T.; Akamatsu, H.; Okamura, K.; Miyagoe, T.; Akiyama, T.; Abe, H.; Takeuchi, Y. J. Chem. Soc., Perkin Trans. 1 2001, 523-528
4. Harayama, T.; Akiyama, T.; Nakano, Y.; Shibaike, K.; Akamatsu, H.; Hori, A.; Abe, H.; Takeuchi, Y. Synthesis 2002, 237-241
5. Bellocchi, D.; Macchiarulo, A.; Costantino, G.; Pellicciari, R. Bioorg. Med. Chem. 2005, 13, 1151-1157
6. Ishida, J.; Hattori, K.; Yamamoto, H.; Iwashita, A.; Mihara, K.; Matsuoka, N. Bioorg. Med. Chem. Lett. 2005, 15, 4221-4225
7. Hartung, C. G.; Fecher, A.; Chapell, B.; Snieckus, V. Org. Lett. 2003, 5, 1899-1902
8. Ganton, M. D.; Kerr, M. A. Org. Lett. 2005, 7, 4777-4779
9. Mentzel, U. V.; Tanner, D.; Tønder, J. E. J. Org. Chem. 2006, 71, 5807-5810
10. Robbins, D. W.; Boebel, T. A.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 4068-4069
11. Umemoto, H.; Dohshita, M.; Hamamoto, H.; Miki, Y. Heterocycles 2011, 83, 1111-1119
12. Zhou, Q. J.; Worm, K.; Dolle, R. E. J. Org. Chem. 2004, 69, 5147-5149
13. Engle, K. M.; Mei, T.-S.; Wasa, M.; Yu, J.-Q. Acc. Chem. Res. 2012, 45, 788-802
14. Patureau, F. W.; Besset, T.; Glorius, F. Angew. Chem., Int. Ed. 2011, 50, 1064-1067
15. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624-655
16. Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651-3678
17. Colby, D. A.; Tsai, A. S.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2012, 45, 814-825
18. Neely, J. M.; Rovis, T. J. Am. Chem. Soc. 2013, 135, 66-69
19. Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792-9826
20. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147-1169
21. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094-5115
22. Miura, H.; Wada, K.; Hosokawa, S.; Inoue, M. Chem.-Eur. J. 2013, 19, 861-864
23. Lian, Y.; Huber, T.; Hesp, K. D.; Bergman, R. G.; Ellman, J. A. Angew. Chem., Int. Ed. 2013, 52, 629-633
24. Wang, N.; Li, B.; Song, H.; Xu, S.; Wang, B. Chem.-Eur. J. 2013, 19, 358-364
25. Pham, M. V.; Ye, B.; Cramer, N. Angew. Chem., Int. Ed. 2012, 51, 10610-10614
26. Tran, D. N.; Cramer, N. Angew. Chem., Int. Ed. 2011, 50, 11098-11102
27. Muralirajan, K.; Parthasarathy, K.; Cheng, C.-H. Angew. Chem., Int. Ed. 2011, 50, 4169-4172
28. Thirunavukkarasu, V. S.; Parthasarathy, K.; Cheng, C.-H. Angew. Chem., Int. Ed. 2008, 47, 9462-9465
29. Thirunavukkarasu, V. S.; Parthasarathy, K.; Cheng, C.-H. Chem.-Eur. J. 2010, 16, 1436-1440
30. Arockiam, P. B.; Bruneau, C.; Dixneuf, P. H. Chem. Rev. 2012, 112, 5879-5918
31. Karthikeyan, J.; Cheng, C.-H. Angew. Chem., Int. Ed. 2011, 50, 98800-9883
32. Karthikeyan, J.; Haridharan, R.; Cheng, C.-H. Angew. Chem., Int. Ed. 2012, 51, 12343-12347
33. Wang, G.-W.; Yuan, T.-T.; Li, D.-D. Angew. Chem., Int. Ed. 2011, 50, 1380-1383
34. Brennfuhrer, A.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 4114-4133
35. Wu, X.-F.; Neumann, H.; Beller, M. Chem. Rev. 2013, 113, 1-35
36. Hasegawa, N.; Charra, V.; Inoue, S.; Fukumoto, Y.; Chatani, N. J. Am. Chem. Soc. 2011, 133, 8070-8073
37. Xie, P.; Xie, Y.; Qian, B.; Zhou, H.; Xia, C.; Huang, H. J. Am. Chem. Soc. 2012, 134, 9902-9905
38. Orito, K.; Horibata, A.; Nakamura, T.; Ushito, H.; Nagasaki, H.; Yuguchi, M.; Yamashita, S.; Tokuda, M. J. Am. Chem. Soc. 2004, 126, 14342-14343
39. Gagnier, S. V.; Larock, R. C. J. Am. Chem. Soc. 2003, 125, 4804-4807
40. Campo, M. A.; Larock, R. C. Org. Lett. 2000, 2, 3675-3677
41. Cao, H.; Alper, H. Org. Lett. 2010, 12, 4126-4129
42. Giri, R.; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 14082-14083
43. Yoo, E. J.; Wasa, M.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 17378-17380
44. Giri, R.; Lam, J. K.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 686-693
45. Inoue, S.; Shiota, H.; Fukumoto, Y.; Chatani, N. J. Am. Chem. Soc. 2009, 131, 6898-6899
46. Du, Y.; Hyster, T. K.; Rovis, T. Chem. Commun. 2011, 47, 12074-12076
47. Wrigglesworth, J. W.; Cox, B.; Lloyd-Jones, G. C.; Booker-Milburn, K. I. Org. Lett. 2011, 13, 5326-5329
48. Zhang, H.; Shi, R.; Gan, P.; Liu, C.; Ding, A.; Wang, Q.; Lei, A. Angew. Chem., Int. Ed. 2012, 51, 5204-5207
49. Chuang, S.-C.; Rajeshkumar, V.; Cheng, C.-A.; Deng, J.-C.; Wang, G.-W. J. Org. Chem. 2011, 76, 1599-1604
50. Chen, C.-P.; Luo, C.; Ting, C.; Chuang, S.-C. Chem. Commun. 2011, 47, 1845-1847
51. Rajeshkumar, V.; Chan, F.-W.; Chuang, S.-C. Adv. Synth. Catal. 2012, 354, 2473-2483
52. Miura, M.; Tsuda, T.; Satoh, T.; Pivsa-Art, S.; Nomura, M. J. Org. Chem. 1998, 63, 5211-5215
53. Liang, Z.; Ju, L.; Xie, Y.; Huang, L.; Zhang, Y. Chem.-Eur. J. 2012, 18, 15816-15821
54. Liu, Y.-Y.; Song, R.-J.; Wu, C.-Y.; Gong, L.-B.; Hu, M.; Wang, Z.-Q.; Xie, Y.-X.; Lia, J.-H. Adv. Synth. Catal. 2012, 354, 347-353
55. Tsang, W. C. P.; Zheng, N.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 14560-14561
56. Li, B.-J.; Tian, S.-L.; Fang, Z.; Shi, Z.-J. Angew. Chem., Int. Ed. 2008, 47, 1115-1118
57. Jordan-Hore, J. A.; Johansson, C. C. C.; Gulias, M.; Beck, E. M.; Gaunt, M. J. J. Am. Chem. Soc. 2008, 130, 16184-16186
58. Cho, S. H.; Yoon, J.; Chang, S. J. Am. Chem. Soc. 2011, 133, 5996-6005
59. Youn, S. W.; Bihn, J. H.; Kim, B. S. Org. Lett. 2011, 13, 3738-3741
60. Urones, B.; Arrayás, R. G.; Carretero, J. C. Org. Lett. 2013, 10.1021/ol400206k
61. Hesp, K. D.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2012, 14, 2304-2307
62. Péron, F.; Fossey, C.; Cailly, T.; Fabis, F. Org. Lett. 2012, 14, 1827-1829
63. Inamoto, K.; Saito, T.; Hiroya, K.; Doi, T. J. Org. Chem. 2010, 75, 3900-3903
64. 2 (1.0 equiv), TFA (1.0 equiv), CO balloon (1 atm), dioxane (1.0 mL), 110 C, 7-65 h. Liang, D.; Hu, Z.; Peng, J.; Huang, J.; Zhu, Q. Chem. Commun. 2013, 49, 173-175