Palladium-catalyzed tandem diperoxidation/C - H activation resulting in diperoxy-oxindole in air

Organic Letters

Volumn 12, Issue 20, 2010, Pages 4482-4485

  An, Guanghui ^a   Zhou, Wei ^a   Zhang, Guangqian ^a   Sun, Hao ^a   Han, Jianlin ^a   Pan, Yi ^a  

^a NANJING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; HYDROGEN; INDOLE DERIVATIVE; OXINDOLE; PALLADIUM; PEROXIDE;

AIR; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; X RAY CRYSTALLOGRAPHY;

AIR; CARBON; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; HYDROGEN; INDOLES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PALLADIUM; PEROXIDES;

EID: 77957839644     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101664y     Document Type: Article

References (39)

1. For reviews, see
2. Rahm, F.; Hayes, P. Y.; Kitching, W. Heterocycles 2004, 64, 523-575
3. Casteel, D. A. Nat. Prod. Rep. 1999, 16, 55-73
4. For artemisinin, see
5. Posner, G. H.; O'Neill, P. M. Acc. Chem. Res. 2004, 37, 397-404
6. Posner, G. H.; Oh, C. H. J. Am. Chem. Soc. 1992, 114, 8328-8329
7. Meshnick, S. R.; Thomas, A.; Ranz, A.; Xu, C. M.; Pan, H. Z. Mol. Biochem. Parasitol. 1991, 49, 181-190
8. For examples of synthesis of peroxides and diperoxides, see
9. Harris, J. R.; Waetzig, S. R.; Woerpel, K. A. Org. Lett. 2009, 11, 3290-3293
10. Lu, X.; Liu, Y.; Sun, B.; Cindric, B.; Deng, L. J. Am. Chem. Soc. 2008, 130, 8134-8135
11. Xiao, Z.; Yao, J.; Yang, D.; Wang, F.; Huang, S.; Gan, L.; Jia, Z.; Jiang, Z.; Yang, X.; Zheng, B.; Yuan, G.; Zhang, S.; Wang, Z. J. Am. Chem. Soc. 2007, 129, 16149-16162
12. Gu, X.; Zhang, W.; Salomon, R. G. J. Am. Chem. Soc. 2007, 129, 6088-6089
13. Schneider, C.; Boeglin, W. E.; Yin, H.; Stec, D. F.; Voehler, M. J. Am. Chem. Soc. 2006, 128, 720-721
14. Cornell, C. N.; Sigman, M. S. J. Am. Chem. Soc. 2005, 127, 2796-2797
15. Yu, J. Q.; Corey, E. J. Org. Lett. 2002, 4, 2727-2730
16. For recent reviews of C - H activation, see
17. Xu, L. M.; Li, B. J.; Yang, Z.; Shi, Z. J. Chem. Soc. Rev. 2010, 39, 712-733
18. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147-1169
19. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624-655
20. Giri, R.; Shi, B. F.; Engle, K. M.; Maugel, N.; Yu, J. Q. Chem. Soc. Rev. 2009, 38, 3242-3272
21. Chen, X.; Engle, K. M.; Wang, D. H.; Yu, J. Q. Angew. Chem., Int. Ed. 2009, 48, 5094-5115
22. Galliford, C. V.; Scheidt, K. A. Angew. Chem. 2007, 119, 8902-8912
23. Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748-8758
24. Marti, C.; Carreira, E. M. Eur. J. Org. Chem. 2003, 2209-2219
25. For synthesis of oxindole via C - H activation methods or related C - C bond formation from C - H bonds, see
26. Ueda, S.; Okada, T.; Nagasawa, H. Chem. Commun. 2010, 46, 2462-2464
27. Perry, A.; Taylor, R. J. K. Chem. Commun. 2009, 3249-3251
28. Miura, T.; Ito, Y.; Murakami, M. Chem. Lett. 2009, 38, 328-329
29. Jiang, T. S.; Tang, R. Y.; Zhang, X. G.; Li, X. H.; Li, J. H. J. Org. Chem. 2009, 74, 8834-8837
30. Jia, Y. X.; Kundig, E. P. Angew. Chem., Int. Ed. 2009, 48, 1636-1639
31. Wasa, M.; Yu, J. Q. J. Am. Chem. Soc. 2008, 130, 14058-14059
32. Pinto, A.; Neuville, L.; Zhu, J. P. Angew. Chem., Int. Ed. 2007, 46, 3291-3295
33. Hennessy, E. J.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 12084-12085
34. Kohno, J.; Koguchi, Y.; Nishio, M.; Nakao, K.; Kuroda, M.; Shimizu, R.; Ohnuki, T.; Komatsubara, S. J. Org. Chem. 2000, 65, 990-995
35. Lee, S.; Hartwig, J. F. J. Org. Chem. 2001, 66, 3402-3415
36. Shaughnessy, K. H.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1998, 63, 6546-6553
37. For recent reviews and application of bioactive 3-hydroxy oxindole, see
38. Peddibhotla, S. Curr. Bioact. Compd. 2009, 5, 20-38
39. Erkizan, H. V.; Kong, Y.; Merchant, M.; Schlottmann, S.; Barber-Rotenberg, J. S.; Yuan, L.; Abaan, O. D.; Chou, T.-H.; Dakshanamurthy, S.; Brown, M. L.; Uren, A.; Toretsky, J. A. Nat. Med. 2009, 15, 750-756