Synthesis of (2-oxoindolin-3-ylidene)methyl acetates involving a C-H functionalization process

Organic Letters

Volumn 10, Issue 9, 2008, Pages 1875-1878

  Tang, Shi ^a,b   Peng, Peng ^a   Wang, Zhi Qiang ^a   Tang, Bo Xiao ^a   Deng, Chen Liang ^a   Li, Jin Heng ^a,c   Zhong, Ping ^a,c   Wang, Nai Xing ^b  

^a WENZHOU UNIVERSITY   (China)

^b HUNAN NORMAL UNIVERSITY   (China)

^c TECHNICAL INSTITUTE OF PHYSICS AND CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; INDOLE DERIVATIVE; METHYL ACETATE; OXINDOLE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMISTRY; SYNTHESIS;

ACETATES; CATALYSIS; INDOLES; PALLADIUM;

EID: 48249110557     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8006315     Document Type: Article

References (45)

1. (a) Mohammadi, M.; McMahon. G.; Sun, L.; Tang, C.; Hirth, P.; Yeh, B. K.; Hubbard, S. R.; Schlessinger, J. Science 1997, 276, 955.
2. (b) Sun, L.; Tran, N.; Liang, C.; Tang, F.; Rice, A.; Schreck, R.; Waltz, K.; Shawver, L. K.; McMahon, G.; Tang, C. J. Med. Chem. 1999, 42, 5120.
3. (c) Hare, B. J.; Walters, W. P.; Caron, P. R.; Bemis, G. W. J. Med. Chem. 2004, 47, 4731.
4. (d) Noble, M. E. M.; Endicott, J. A.; Johnson, L. N. Science 2004, 203. 1800.
5. (e) Liao, J. J.-L. J. Med. Chem. 2007, 50, 409.
6. (f) Drugs Future 1990, 15898.
7. (g) Robinson, R. P.; Reiter. L. A.; Barth, W. E.; Campeta, A. M.; Cooper, K.; Cronin, B. J.; Destito, R.; Donahue, K. M.; Falkner, F. C.; Fiese, E. F.; Johnson, D. L.; Kuperman, A. V.; Liston, T. E.; Malloy, D.; Martin, J. J.; Mitchell, D. Y.; Rusek, F. W.; Shamblin, S. L.; Wright, C. F. J. Med. Chem. 1996, 39, 10.
8. (h) Bramson, H. N.; Corona, J.; Davis, S. T.; Dickerson, S. H.; Edelstein, M.; Frye, S. V.; Gampe, R. T., Jr.; Harris, P. A.; Hassell, A.; Holmes, W. D.; Hunter, R. N.; Lackey, K. E.;L ovejoy, B.; Luzzio, M. J.; Montana, V.; Rocque, W. J.; Rusnak, D.; Shewchuk, L.; Veal, J. M.; Walker, D. H.; Kuyper. L. F. J. Med. Chem. 2001, 44, 4339.
9. (i) Graczyk, P. P. J. Med. Chem. 2007, 50, 5773.
10. (a) Mori, M.; Ban, Y. Tetrahedron Lett. 1979, 20, 1133.
11. (b) Sun, L.; Liang. C.; Shirazian. S.; Zhou, Y.; Miller, T.; Cui, J.; Fukuda, J. Y.; Chu, J.-Y.; Nematalla, A.; Wang, X.; Chen, H.; Sistla, A.; Luu, T. C.; Tang, F.; Wei, J.; Tang, C. J. Med. Chem. 2003, 46, 1116.
12. (c) Wang, L.; Zhang, Y.; Hu, H.-Y.; Fun, H. K.; Xu, J.-H. J. Org. Chem. 2005, 70, 3805.
13. (d) Kalinski, C.; Umkehrer, M.; Schmidt, J.; Ross, G.; Kolb, J.; Burdack, C.; Hiller, W.; Hoffmann, S. D. Tetrahedron Lett. 2006, 47, 4683.
14. (e) Xing, X.; Wu, J.; Luo, J.; Dai, W.-M. Synlett 2006, 2099.
15. (f) Yang, T.-M.; Liu, G. J. Comb. Chem. 2007, 9, 86.
16. Pd: (a) Cheung, W. S.; Patch, R. J.; Player, M. R. J. Org. Chem. 2005, 70, 3741.
17. (b) Yanada, R.; Obika, S.; Inokuma, T.; Yanada. K.; Yamashita, M.; Ohta, S.; Takemoto, Y. J. Org. Chem, 2005, 70, 6972.
18. (c) Pinto, A.; Neuville, L.; Retailleau, P.; Zhu, J. Org. Lett. 2006, 8, 4927.
19. (d) Pinto, A.; Neuville, L.; Zhu, J. Angew. Chem., Int. Ed. 2007, 46, 3291.
20. (e) Couty, S.; Liégault, B.; Meyer, C.; Cossy, J. Org. Lett. 2004, 6, 2511.
21. (f) D'Souza, D. M.; Rominger, F.; Müller, T. J. J. Angew. Chem., Int. Ed. 2005, 44, 153.
22. (g) Tang, S.; Yu, Q.-F.; Peng, P.; Li, J.-H.; Zhong, P.; Tang, R.-Y. Org. Lett. 2007, 9, 3413. In/Pd:
23. (h) Yanada, R.; Obika. S.; Oyama,M.; Takemoto, Y. Org. Lett. 2004, 6, 2825. Rh:
24. (i) Shintani, R.; Yamagami, T.; Hayashi, T. Org. Lett. 2006, 8, 4799.
25. (j) Miura, T.; Takahashi, Y.; Murakami, M. Org. Lett. 2007, 8, 5075.
26. Tang, S.; Peng, P.; Pi. S.-F.; Liang, Y.; Wang, N.-X.; Li, J.-H. Org. Lett. 2008, 10, 1179.
27. The detailed experimental data are summarized in Table S1 in Supporting Information.
28. The structure of the products and the E-configuration of the tetrasubstituted double bond were determined according to the COSY and NOESY of the products 12 and 16 and were unambiguously assigned by X-ray analysis of the products 9 and 14 (see Supporting Information).
29. VI process, see:
30. (a) Yu. J.-Q.; Giri, R.; Chen. X. Org. Biatrial. Chem. 2006. 4, 4042.
31. (b) Deprez, N. R.; Sanford, M. S. Inorg. Chem. 2007, 46, 1924.
32. (c) Deprez, N. R.; Kalyani, D.: Krause, A.; Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 4972.
33. (d) Hull, K. L.; Lanni, E. L.; Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 14047.
34. (e) Kalyani, D.; Dick, A. R.; Anani, W. Q.; Sanford, M. S. Org. Lett. 2006, 8, 2523.
35. (f) Thu, H.-Y.; Yu, W.-Y.; Che, C.-M. J. Am. Chem. Soc. 2006, 128, 9048.
36. (g) Liu, G.; Stahi, S. S. J. Am. Chem. Soc. 2006. 128, 7179.
37. (h) Tong, X.; Beller, M.; Tse, M. K. J. Am. Chem. Soc. 2007, 129. 4906.
38. (i) Welbes, L. L.; Lyons, T. W.; Cvchosz, K. A.; Sanford, M. S. J. Am. Chem. Soc. 2007, 129, 5836.
39. (j) Whitfield, S. R.; Sanford, M. S. J. Am. Chem. Soc. 2007, 129, 15142.
40. (k) Muniz, K. J. Am. Chem. Soc. 2007, 129, 14542.
41. Muniz, K.; Hovelmann, C. H.; Streuff, J. J. Am. Chem. Soc. 2008, 130, 763.
42. 2 combined with the specified additives in the reaction of 1. Lu, X.; Zhu, G.; Ma, S. Tetrahedron Lett. 1992, 33, 7205.
43. (b) Wakabayashi, T.; Ishii, Y.; Murata, T.; Mizobe, Y.; Hidai, M. Tetrahedron Lett. 1995. 36, 5585.
44. (c) Han, X. L.; Liu, G. X.; Lu, X. Y. Chin. J. Org. Chem. 2005, 25, 1182.
45. The results of the kinetic isotope effect are summarized in the Supporting Information.