Palladium-catalyzed domino N-arylation/carbopalladation/C-H functionalization: three-component synthesis of 3-(diarylmethylene)oxindoles

Tetrahedron Letters

Volumn 50, Issue 26, 2009, Pages 3602-3605

  Pinto, Artur ^a   Neuville, Luc ^a   Zhu, Jieping ^a  

^a CNRS   (France)

Author keywords

C H activation; Carbopalladation; Multicomponent reaction; N Arylation; Oxindole; Palladium

Indexed keywords

INDOLE DERIVATIVE; OXINDOLE; PALLADIUM;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; ONE POT SYNTHESIS; SUBSTITUTION REACTION;

EID: 65549088656     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.03.086     Document Type: Article

References (47)

1. Sun L., Tran N., Tang F., App H., Hirth P., McMahon G., and Tang C. J. Med. Chem. 41 (1998) 2588-2603
2. Hauf S., Cole R.W., Laterra S., Zimmer C., Schnapp G., Walter R., Heckel A., van Meel J., Rieder C.L., and Peters J.M. J. Cell. Biol. 161 (2003) 281-294
3. Noble M.E.M., Endicott J.A., and Johnson L.N. Science 303 (2004) 1800-1805
4. Indium-promoted. Yanada R., Obika S., Oyama M., and Takemoto Y. Org. Lett. 6 (2004) 2825-2828
5. Yanada R., Obika S., Inokuma T., Yanada K., Yamashita M., Ohta S., and Takemoto Y. J. Org. Chem. 70 (2005) 6972-6975
6. Palladium-catalyzed. D'Souza D.M., Rominger F., and Müller T.J.J. Angew. Chem., Int. Ed. 44 (2005) 153-158
7. Cheung W.S., Patch R.J., and Player M.R. J. Org. Chem. 70 (2005) 3741-3744
8. Dai W.M., Shi J., and Wu J. Synlett (2008) 2716-2720
9. Rhodium-catalyzed. Shintani R., Yamagami T., and Hayashi T. Org. Lett. 8 (2006) 4799-4801
10. Palladium-catalyzed. Kamijo S., Sasaki Y., Kanazawa C., Schüsseler T., and Yamamoto Y. Angew. Chem., Int. Ed. 44 (2005) 7718-7721
11. Miaura T., Toyoshima T., Takahashi Y., and Murakami M. Org. Lett. 10 (2008) 4887-4889
12. Rhodium-catalyzed. Miura T., Takahashi Y., and Murakami M. Org. Lett. 9 (2007) 5075-5077
13. Tang S., Yu Q.-F., Peng P., Li J.-H., Zhong P., and Tang R.-Y. Org. Lett. 9 (2007) 3413-3416
14. See also. Marcaccini S., Pepino R., Marcos C.F., Polo C., and Torroba T. J. Heterocycl. Chem. (2000) 1501-1503
15. Wang L., Zhang Y., Hu H.-Y., Fun H.K., and Xu J.-H. J. Org. Chem. 70 (2005) 3850-3858
16. Pinto A., Neuville L., Retailleau P., and Zhu J. Org. Lett. 8 (2006) 4927-4930
17. Tang S., Peng P., Pi S.F., Liang Y., Wang N.X., and Li J.H. Org. Lett. 10 (2008) 1179-1182
18. Tang S., Peng P., Wang Z.Q., Tang B.X., Deng C.L., Li J.H., Zhong P., and Wang N.X. Org. Lett. 10 (2008) 1875-1878
19. Tang S., Peng P., Zhong P., and Li J.H. J. Org. Chem. 73 (2008) 5476-5480
20. Pinto A., Neuville L., and Zhu J. Angew. Chem., Int. Ed 46 (2007) 3291-3295
21. Bonnaterre F., Bois-Choussy M., and Zhu J. Org. Lett. 8 (2006) 4351-4354
22. Pinto A., Jia X., Neuville L., and Zhu J. Chem. Eur. J. 13 (2007) 961-967
23. Cuny G., Bois-Choussy M., and Zhu J. Angew. Chem., Int. Ed. 42 (2003) 4774-4777
24. Cuny G., Bois-Choussy M., and Zhu J. J. Am. Chem. Soc. 126 (2004) 14475-14484
25. Salcedo A., Neuville L., Rondot C., Retailleau P., and Zhu J. Org. Lett. 10 (2008) 857-860
26. Gerfaud T., Neuville L., and Zhu J. Angew. Chem., Int. Ed. 48 (2009) 572-577
27. Reviews on metal-catalyzed multicomponent reactions. Balme G., Bossharth E., and Monteiro N. Eur. J. Org. Chem. (2003) 4101-4111
28. Murakami M. Angew. Chem., Int. Ed. 42 (2003) 718-720
29. D́Souza D.M., and Müller T.J.J. Chem. Soc. Rev. 36 (2007) 1095-1108
30. Arndtsen B.A. Chem. Eur. J. 15 (2009) 302-312
31. Müller T.J.J. Top. Organomet. Chem. 19 (2006) 149-205
32. Hartwig J.F. In: Negishi E.-I., and de Meijere A. (Eds). Handbook of Organopalladium Chemistry for Organic Synthesis Vol. 1 (2002), Wiley-Interscience, New York 1051-1096
33. Muci A.R., and Buchwald S.L. Top Curr. Chem. 219 (2002) 133-205
34. Yin J., and Buchwald S.L. Org. Lett. 2 (2000) 1101-1104
35. We have previously determined that DMF is a solvent of choice for the carbopalladation/C-H functionalization sequence, see Ref. 6.
36. Leclerc J.-P., André M., and Fagnou K. J. Org. Chem. 71 (2006) 1711-1714 and references therein.
37. Lira R., and Wolfe J.P. J. Am. Chem. Soc. 126 (2004) 13906-13907
38. Lipshutz B.H., Frieman B., and Birkedal H. Org. Lett. 6 (2004) 2305-2308
39. 3 ([M+Na]+) 379.1059, found 379.1052.
40. White D.A., and Baizer M.M. Tetrahedron Lett. 14 (1973) 3597-3600
41. The stability of E- and Z-isomers depends on the substitution pattern of oxindoles. In previous studies, we observed that E/Z isomerization readily occurred with N-methyl-5-nitro-3-[phenyl)(2'-nitophenyl)methylene]indolin-2-one. See Ref. 6.
42. Zargarian D., and Alper H. Organometallics 10 (1991) 2914-2921
43. Dyker G., and Kellner A. Tetrahedron Lett. 35 (1994) 7633-7636
44. de Vaal P., and Dedieu A. J. Organomet. Chem. 478 (1994) 121-129
45. Gibbs R.A., Krishnan U., Dolence J.M., and Poulter C.D. J. Org. 60 (1995) 7821-7829
46. Ji J., Wang Z., and Lu X. Organometallics 15 (1996) 2821-2828
47. Arcadi A., Cacchi S., Fabrizi G., and Marinelli P.P. Eur. J. Org. Chem. (1999) 3305-3313