Palladium-catalyzed sp3 C-H activation of simple alkyl groups: Direct preparation of indoline derivatives from N-alkyl-2-bromoanilines

Organic Letters

Volumn 10, Issue 9, 2008, Pages 1759-1762

  Watanabe, Toshiaki ^a   Oishi, Shinya ^a   Fujii, Nobutaka ^a   Ohno, Hiroaki ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE DERIVATIVE; INDOLE DERIVATIVE; INDOLINE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMISTRY; SYNTHESIS;

ANILINE COMPOUNDS; CATALYSIS; INDOLES; PALLADIUM;

EID: 48849113342     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800425z     Document Type: Article

References (53)

1. For recent reviews, see: (a) Shilov, A. E.; Shul'pin, G. B, Chem. Rev. 1997, 97, 2879.
2. (b) Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698.
3. (c) Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633.
4. For recent reviews, see: (a) Crabtree, R. H. J. Organomet. Chem. 2004, 689, 4083.
5. (b) Kakiuchi, F.: Chatani, N. Adv. Synth. Catal. 2003, 345, 1077.
6. 2 C-H activation, see:
7. (a) Campeau, L.-C; Parisien, M.; Jean, A.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 581.
8. (b) Garcia-Cuadrado, D.; Mendoza, P.; Braga, A. A. C.; Maseras, F.; Echavarren. A. M. J. Am. Chem. Soc. 2007, 129, 6880.
9. (c) Terao, Y.; Wakui, H.: Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2001,123, 10407.
10. (d) Lafrance, M.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 16496.
11. (a) For our related works, see: Ohno, H.; Miyamura, K.; Takeoka, Y.; Tanaka, T. Angew. Chem., Int. Ed. 2003, 42, 2647.
12. (b) Ohno, H.; Yamamoto, M.; Iuchi, M.; Tanaka, T. Angew. Chem., Int. Ed. 2005, 44, 5103.
13. (c) Watanabe. T.; Ueda, S.; Inuki, S.; Oishi, S.; Fujii, N.; Ohno, H. Chem. Commun. 2007,43, 4516.
14. (d) Ohno, H.: Iuchi, M.; Fujii, N.; Tanaka, T. Org. Lett. 2007, 9, 4813.
15. (a) Dong, C.-G.; Hu, Q.-S. Angew. Chem., Int. Ed. 2006, 45, 2289.
16. (b) Ren, H.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 3462.
17. (c) Ren. H.; Li, Z.; Knochel, P. Chem. Asian. J. 2007, 2, 416.
18. (a) Dyker, G. Angew. Chem., Int. Ed. 1992, 31, 1023.
19. (b) Dyker, G. J. Org. Chem. 1993, 58, 6426.
20. (c) DeBoef, B.; Pastine. S. J.; Sanies, D. J. Am. Chem. Soc. 2004, 126, 6556.
21. (d) Li, Z.; Bohle, D. S.: Li, C.-J. Proc. Natl. Acad. Sci. U. S. A. 2006, 103, 8928.
22. (e) Pastine, S. J.; Gribkov, D. V.; Sames, D. J. Am. Chem. Soc. 2006, 128, 14220.
23. 3 C-H activation of simple alkanes without using any assisting groups in the substrate, see: Chen, H.; Schlecht, S.; Semple, T. C; Hartwig, J. F. Science 2000, 287, 1995.
24. (a) Jun, C-H.; Hwang, D.-C; Na, S.-J. Chem. Commun. 1998. 1405.
25. (b) Chatani. N.; Asaumi, T.; Yorimitsu, S.; Ikeda, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 2001, 123, 10935.
26. (c) Kalyani, D.; Deprez, N. R.; Desai, L. V.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 7330.
27. (d) Shabashov, D.; Daugulis, O. Org. Lett. 2005, 7, 3657.
28. (e) Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2005,127, 13154.
29. (f) Reddv, B. V. S.; Reddy, L. R.; Corey, E. J. Org. Lett. 2006, 8, 3391.
30. (g) Chen, X.; Goodhue, C. E.; Yu, J.-Q J. Am. Chem, Soc. 2006, 128, 12634.
31. (h) For pyridine- or oxime-assisted reactions, see: Desai. L. V.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 9542.
32. (a) Dyder, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 103.
33. (b) Baudoin, O.; Herrbach. A.; Guéritte, F. Angew. Chem., Int. Ed. 2003, 42, 5736.
34. (c) Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005. 127, 4685.
35. (d) Hitce, J.; Retailleau. P.; Baudoin, O. Chem. Eur. J. 2007, 13, 792.
36. (e) Giri, R.; Maugel, N.; Li, J.-J.; Wang, D.-H.; Breazzano, S. P.; Saunders, L. B.; Yu, J.-Q. J. Am. Chem. Soc. 2007. 129. 3510.
37. (f) Lafrance, M; Gorelsky, S. I.; Fagnou, K. J. Am. Chem. Soc. 2007, 129, 14570.
38. (a) Llabres, J. M.; Viladomat, F.; Bastida, J.; Codina, C; Rubiralta. M. Photochemistry 1986, 25, 2637.
39. (b) Ghosal, S.; Rao, P. H.; Jaiswal. D. K.; Kumar, Y.;'Frahm, A. W. Phytochemistry 1981, 20, 2003.
40. (c) Kam, T.-S.; Subramaniam, G.; Lim, K.-H.; Choo. Y.-M. Tetrahedron Lett. 2004. 45, 5995.
41. For synthesis of indolines, see:
42. (a) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1999, 38, 2426.
43. (b) Thansandote, P.; Raemy, M.; Rudolph, A.; Lautens, M Org. Lett. 2007, 9, 5255, and references therein.
44. 3 C-H activation of 2-tert-butoxy-bromobenzene in the presence of pivalic acid and its related substrates to form 2,2-dialkyldihydrobenzofurans has appeared in the literature: see ref 9f. Mechanistic consideration as well as the effect of pivalic acid based on DFT calculations was also reported.
45. This phosphonium salt was used because it is more stable than the corresponding free phosphine.
46. Decreased yield in entry 2 can be attributed to catalyst poisoning by the iodide anion, see for example: Campeau, L.-C; Parisien, M.; Jean, A.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 581.
47. (a) The unsuccessful result with the N-unprotected substrate 5a might be due to the formation of the four-membered azapalladacycle 18. For related azapalladacycles, see: Solé, D.; Serrano, O. Angew. Chem., Int. Ed. 2007, 46, 7270.
48. (b) Solé, D.: Vallverdú, L.; Solans, X.; Font-Bardia, M.; Bonjoch, J. J. Am. Chem. Soc. 2003, 125, 1587.
49. (c) See also: Gies, A.-E.; Pfeffer, M.; Sirlin, C; Spencer, J. Eur. J. Org. Chem, 1999, 8, 1957.
50. (d) Vicente, J.; Abad, J.-A.; Frankland, A. D.; Ramírez de Arellano, M. C. Chem. Eur. J. 1999, 5, 3066.
51. (a) Related aza-oxindole derivatives are known as potent kinase inhibitors, see : Adams, C; Aldous, D. J.; Amendola, S.; Bamborough, P.; Bright, C; Crowe, S.; Eastwood, P.; Fenton, G.; Foster, M.; Harrison, T. K. P.; King, S.; Lai, J.; Lawrence, C; Letallec, J.-P.; McCarthy, C; Moorcroft, N.; Page, K.; Rao, S.; Redford, J.; Sadiq, S.; Smith, K.; Souness, J, E.; Thurairatnam, S.; Vine, M,; Wyman, B. Bioorg. Med. Chem. Lett. 2003, 13. 3105.
52. (b) Wood, E. R.; Kuyper, L.; Petrov, K. G.; Hunter, R. N.; Harris, P. A.: Lackey, K. Bioorg. Med. Chem. Lett. 2004, 14, 953.
53. For a related C-H activation of an isopropyl group assisted by a quaternary carbon, see ref 9d.