Palladium-catalyzed three-component synthesis of 3-(diarylmethylene) oxindoles through a domino sonagashira/carbopalladation/C-H activation/C-C bond-forming sequence

Angewandte Chemie - International Edition

Volumn 46, Issue 18, 2007, Pages 3291-3295

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

^a CNRS   (France)

Author keywords

C H activation; Domino reactions; Multicomponent reactions; Nitrogen heterocycles; Palladium

Indexed keywords

ACTIVATION ENERGY; CATALYST ACTIVITY; CHEMICAL BONDS; PALLADIUM; REACTION KINETICS;

CATALYTIC CYCLES; INTERMOLECULAR CARBOPALLADATION; SONAGASHIRA REACTION;

KETONES;

EID: 34250838053     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200605192     Document Type: Article

References (76)

1. Multicomponent Reactions (Eds.: J. Zhu, H. Bienaymé), Wiley-VCH, Weinheim, 2005.
2. a) B. M. Trost, Angew. Chem. 1995, 107, 285-307;
3. Angew. Chem. Int. Ed. Engl. 1995, 34, 259-281;
4. b) P. A. Wender, S. T. Handy, D. L. Wright, Chem. Ind. 1997, 765-769.
5. L. Banfi, R. Riva, Org. React. 2005, 65, 1-140.
6. a) A. Dömling, I. Ugi, Angew. Chem. 2000, 112, 3301-3344;
7. Angew. Chem. Int. Ed. 2000, 39, 3168-3210;
8. b) J. Zhu, Eur. J. Org. Chem. 2003, 1133-1144;
9. c) A. Dömling, Chem. Rev. 2006, 106, 17-89.
10. General reviews on domino process: a) L. F. Tietze, Chem. Rev. 1996, 96, 115-136;
11. b) K. C. Nicolaou, D. J. Edmonds, P. G. Bulger, Angew. Chem. 2006, 118, 7292-7344;
12. Angew. Chem. Int. Ed. 2006, 45, 7134-7186.
13. For a recent book, see: Domino Reactions in Organic Synthesis (Eds.: L. F. Tietze, G. Brasche, K. Gericke), Wiley-VCH, Weinheim, 2006.
14. a) G. Cuny, M. Bois-Choussy, J. Zhu, Angew. Chem. 2003, 115, 4922-4925;
15. Angew. Chem. Int. Ed. 2003, 42, 4774-4777;
16. b) G. Cuny, M. Bois-Choussy, J. Zhu, J. Am. Chem. Soc. 2004, 126, 14 475-14 484;
17. c) A. Pinto, X. Jia, L. Neuville, J. Zhu, Chem. Eur. J. 2007, 13, 961-967.
18. Reviews on C-H activation: a) A. D. Ryabov, Chem. Rev. 1990, 90, 403-424;
19. b) G. Dyker, Angew. Chem. 1999, 111, 1808-1822;
20. Angew. Chem. Int. Ed. 1999, 38, 1698-1712;
21. c) C. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem. Res. 2001, 34, 633-639;
22. d) M. Miura, M. Nomura, Top. Curr. Chem. 2002, 219, 211-241;
23. e) V. Ritleng, C. Sirlin, M. Pfeffer, Chem. Rev. 2002, 102, 1731-1770;
24. f) F. Kakiuchi, S. Murai, Acc. Chem. Res. 2002, 35, 826-834;
25. g) C.-J. Li, Acc. Chem. Res. 2002, 35, 533-538;
26. h) M. Catellani, Synlett 2003, 298-313;
27. i) L.-C. Campeau, K. Fagnou, Chem. Commun. 2006, 1253-1264;
28. j) D. Alberico, M. E. Scott, M. Lantens, Chem. Rev. 2007, 107, 174-238.
29. Indium-mediated cyclization/Pd-catalyzed cross-coupling: R. Yanada, S. Obika, M. Oyama, Y. Takemoto, Org. Lett. 2004, 6, 2825-2828.
30. Pd-catalyzed Heck cyclization/Suzuki-Miyaura coupling: a) W. S. Cheung, R. J. Patch, M. R. Player, J. Org. Chem. 2005, 70, 3741-3744;
31. b) R. Yanada, S. Obika, T. Inokuma, K. Yanada, M. Yamashita, S. Ohta, Y. Takemoto, J. Org. Chem. 2005, 70, 6972-6975.
32. Pd-catalyzed Heck cyclization/Sonogashira coupling: D. M. D'Souza, F. Rominger, T. J. J. Müller, Angew. Chem. 2005, 117, 156-161;
33. Angew. Chem. Int. Ed. 2005, 44, 153-158.
34. Rhodium-catalyzed carbopalladation/cross-coupling: R. Shintani, T. Yamagami, T. Hayashi, Org. Lett. 2006, 8, 4799-4801.
35. S. Kamijo, Y. Sasaki, C. Kanazawa, T. Schusseler, Y. Yamamoto, Angew. Chem. 2005, 117, 7896-7899;
36. Angew. Chem. Int. Ed. 2005, 44, 7718-7721.
37. a) M. E. M. Noble, J. A. Endicott, L. N. Johnson, Science 2004, 303, 1800-1805;
38. b) A. Andreani, S. Burnelli, M. Granaiola, A. Leoni, A. Locatelli, R. Morigi, M. Rambaldi, L. Varoli, M. W. Kunkel, J. Med. Chem. 2006, 49, 6922-6924, and references therein.
39. a) K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 1975, 16, 4467-4770;
40. b) E. Negishi, L. Anastasia, Chem. Rev. 2003, 103, 1979-2018.
41. A. Pinto, L. Neuville, P. Retailleau, J. Zhu, Org. Lett. 2006, 8, 4927-4930.
42. Intramolecular carbopalladation, C-H activation, and C-C bond-forming processes: a) S. M. Abdur Rahman, M. Sonoda, K. Itahashi, Y. Tobe, Org. Lett. 2003, 5, 3411-3414;
43. b) H. Ohno, M. Yamamoto, M. Iuchi, T. Tanaka, Angew. Chem. 2005, 117, 5233-5236;
44. Angew. Chem. Int. Ed. 2005, 44, 5103-5106;
45. c) L. F. Tietze, F. Lotz, Eur. J. Org. Chem. 2006, 4676-4684.
46. Recent reviews: a) G. Poli, G. Giambastiani, A. Heumann, Tetrahedron 2000, 56, 5959-5989;
47. b) S.-I. Ikeda, Acc. Chem. Res. 2000, 33, 511-519;
48. c) I. Nakamura, Y. Yamamoto, Chem. Rev. 2004, 104, 2127-2198;
49. d) G. Zeni, R. Larock, Chem. Rev. 2004, 104, 2285-2310;
50. e) J.-C. Wasilke, S. J. Obrey, R. T. Baker, G. C. Bazan, Chem. Rev. 2005, 105, 1001-1020;
51. f) S. Cacchi, G. Fabrizi, Chem. Rev. 2005, 105, 2873-2920;
52. g) G. Zeni, R. Larock, Chem. Rev. 2006, 106, 4644-4680.
53. Tandem catalysis reviews: a) A. Ajamian, J. L. Gleason, Angew. Chem. 2004, 116, 3842-3848;
54. Angew. Chem. Int. Ed. 2004, 43, 3754;
55. b) D. E. Fogg, E. N. Santos, Coord. Chem. Rev. 2004, 248, 2365-2379;
56. c) J. M. Lee, Y. Na, H. Han, S. Chang, Chem. Soc. Rev. 2004, 33, 302-312;
57. d) J.-C. Wasilke, S. J. Obrey, R. T. Baker, G. C. Bazan, Chem. Rev. 2005, 105, 1001-1020.
58. Reviews on metal-catalyzed multicomponent reactions: a) G. Balme, E. Bossharth, N. Monteiro, Eur. J. Org. Chem. 2003, 4101-4111;
59. b) M. Murakami, Angew. Chem. 2003, 115, 742-744;
60. Angew. Chem. Int. Ed. 2003, 42, 718-720.
61. Multicomponent reactions involving a key Sonogashira reaction: a) T. J. J. Müller, M. Ansorge, D. Aktah, Angew. Chem. 2000, 112, 1323-1326;
62. Angew. Chem. Int. Ed. 2000, 39, 1253-1256;
63. b) C. J. Kressierer, T. J. J. Müller, Angew. Chem. 2004, 116, 6123-6127;
64. Angew. Chem. Int. Ed. 2004, 43, 5997-6000;
65. c) A. S. Karpov, E. Merkul, F. Rominger, T. J. J. Müller, Angew. Chem. 2005, 117, 7112-7117;
66. Angew. Chem. Int. Ed. 2005, 44, 6951-6956;
67. d) L. R. Pottier, J.-F. Peyrat, M. Alami, J.-D. Brion, Synlett 2004, 1503-1508;
68. synthesis of tetrasubstituted olefines by a carbopalladation-initiated MCR: e) C. Zhou, R. C. Larock, J. Org. Chem. 2005, 70, 3765-3777.
69. a) T. Eckert, J. Ipaktschi, Synth. Commun. 1998, 28, 327-335;
70. for alternatives, see: b) L. Anastasia, E.-I. Negishi, Org. Lett. 2001, 3, 3111-3113;
71. c) U. Radhakrishnan, P. J. Stang, Org. Lett. 2001, 3, 859-860.
72. a) L. A. Hay, T. M. Keonig, F. O. Ginah, J. D. Copp, D. Mitchell, J. Org. Chem. 1998, 63, 5050-5058;
73. b) A. Arnautu, V. Collot, J. C. Ros, C. Alayrac, B. Witulski, S. Rault, Tetrahedron Lett. 2002, 43, 2695-2697.
74. Recent examples of Cu-free Sonogashira reactions: a) C. Yi, R. Hua, J. Org. Chem. 2006, 71, 2535-2537;
75. b) A. Tougerti, S. Negri, A. Jutand, Eur. J. Org. Chem. 2007, 666-676, and references therein.
76. J.-P. Leclerc, M. André, K. Fagnou, J. Org. Chem. 2006, 71, 1711-1714, and references therein.