Palladium-catalyzed, modular synthesis of highly functionalized indoles and tryptophans by direct annulation of substituted o-haloanilines and aldehydes

Journal of Organic Chemistry

Volumn 71, Issue 20, 2006, Pages 7826-7834

  Jia, Yanxing ^a   Zhu, Jieping ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CATALYSIS; PALLADIUM; REACTION KINETICS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

MODULAR SYNTHESIS; O-HALOANILINES; RACEMIZATION; TRYPTOPHANS;

NITROGEN COMPOUNDS;

2 N,N DI TERT BUTOXYCARBONYL 5 OXOPENTANOATE; ALDEHYDE DERIVATIVE; ANILINE DERIVATIVE; GLUTAMIC ACID DERIVATIVE; HALOALDEHYDE; INDOLE DERIVATIVE; PALLADIUM; TRYPTOPHAN DERIVATIVE; UNCLASSIFIED DRUG; VALERIC ACID DERIVATIVE;

ANNULATION REACTION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ORGANIC CHEMISTRY; RACEMIZATION; STRUCTURE ANALYSIS; SYNTHESIS;

ALDEHYDES; ANILINE COMPOUNDS; CATALYSIS; INDOLES; PALLADIUM; TRYPTOPHAN;

EID: 33749158251     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061471s     Document Type: Article

References (115)

1. For recent reviews on indole-containing natural products, see: (a) Somei, M.; Yamada, F. Nat. Prod. Rep. 2004, 21, 278-311.
2. (b) Somei, M.; Yamada, F. Nat. Prod. Rep. 2005, 22, 73-103.
3. (c) Kawasaki, T.; Higuchi, K. Nat. Prod. Rep. 2005, 22, 761-793.
4. For leading references on the physiological activity of indole derivatives, see: (d) Van Zandt, M. C.; Jones, M. L.; Gunn, D. E.; Geraci, L. S.; Jones, J. H.; Sawicki, D. R.; Sredy, J.; Jacot, J. L.; DiCioccio, A. T.; Petrova, T.; Mitschler, A.; Podjarny, A. D. J. Med. Chem. 2005, 48, 3141-3152.
5. For recent references on the total synthesis of indole alkaloids, see: (e) Herzon, S. B.; Myers, A. G. J. Am. Chem. Soc. 2005, 127, 5342-5344.
6. (f) Baran, P. S.; Guerrero, C. A.; Hafensteiner, B. D.; Ambhaikar, N. B. Angew. Chem., Int. Ed. 2005, 44, 3892-3895.
7. (g) Yamashita, T.; Kawai, N.; Tokuyama, H.; Fukuyama, T. J. Am. Chem. Soc. 2005, 127, 15038-15039.
8. Gribble, G. W. Contemp. Org. Synth. 1994, 1, 145-172.
9. For a recent general review on the construction of the indole ring, see: Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000, 1045-1075.
10. For recent reports on indoles synthesis without a Pd catalyst, see: (a) Arisawa, M.; Terada, Y.; Nakagawa, M.; Nishida, A. Angew. Chem., Int. Ed. 2002, 41, 4732-4734.
11. (b) Coleman, C. M.; O'Shea, D. F. J. Am. Chem. Soc. 2003, 125, 4054-4055.
12. (c) Shimada, T.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 10546-10547.
13. (d) Dunetz, J. R.; Danheiser, R. L. J. Am. Chem. Soc. 2005, 127, 5776-5777.
14. (e) Taber, D. F.; Tian, W. J. Am. Chem. Soc. 2006, 128, 1058-1059.
15. (f) Davies, H. M. L.; Manning, J. R. J. Am. Chem. Soc. 2006, 128, 1060-1061.
16. For reviews on palladium-catalyzed synthesis of indoles, see: (a) Hegedus, L. S. Angew. Chem., Int. Ed. 1988, 27, 1113-1126.
17. (b) Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285-2309.
18. (c) Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127-2198.
19. (d) Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079-3160.
20. (e) Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873-2920.
21. For recent reports on Pd-catalyzed indole synthesis, see: (a) Rutherford, J. L.; Rainka, M. P.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 15168-15169.
22. (b) Siebeneicher, H.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. 2003, 42, 3042-3044.
23. (c) Willis, M. C.; Brace, G. N.; Holmes, I. P. Angew. Chem., Int. Ed. 2005, 44, 403-406.
24. (d) Barluenga, J.; Fernandez, M. A.; Aznar, F.; Valdés, C. Chem. - Eur. J. 2005, 11, 2276-2283.
25. (e) Fang, Y.-Q.; Lautens, M. Org. Lett. 2005, 7, 3549-3552.
26. (f) Mukai, C.; Takahashi, Y. Org. Lett. 2005, 7, 5793-5796.
27. (a) Heck, R. F. Org. React. 1982, 27, 345-390.
28. (b) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379-2411.
29. (c) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009-3066.
30. (d) Amatore, C.; Jutard, A. Acc. Chem. Res. 2000, 33, 314-321.
31. (e) Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945-2964.
32. Mori, M.; Chiba, K.; Ban, Y. Tetrahedron Lett. 1977, 1037-1040.
33. Odle, R.; Blevins, B.; Ratcliff, M.; Hegedus, L. S. J. Org. Chem. 1980, 45, 2709-2710.
34. For a review, see: Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671-2681.
35. (a) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689-6690.
36. (b) Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652-7662.
37. (c) Roesch, K. R.; Larock, R. C. J. Org. Chem. 2001, 66, 412-420.
38. (d) From ortho-chloroaniline, see: Shen, M.; Li, G.; Lu, B. Z.; Hossain, A.; Roschangar, F.; Farina, V.; Senanayake, C. H. Org. Lett. 2004, 6, 4129-4132.
39. Iida, H.; Yuasa, Y.; Kibayashi, C. J. Org. Chem. 1980, 45, 2938-2942.
40. Michael, J. P.; Chang, S.-F.; Wilson, C. Tetrahedron Lett. 1993, 34, 8365-8368.
41. (b) Chen, L.-C.; Yang, S.-C.; Wang, H.-M. Synthesis 1995, 385-386.
42. (c) Watanabe, T.; Arai, S.; Nishida, A. Synlett 2004, 907-909.
43. (a) Koerber-Plé, K.; Massiot, G. Synlett 1994, 759-760.
44. (b) For solid phase synthesis, see: Yamazaki, K.; Nakamura, Y.; Kondo, Y. J. Org. Chem. 2003, 68, 6011-6019.
45. Sakamoto, T.; Nagano, T.; Kondo, Y.; Yamanaka, H. Synthesis 1990, 215-218.
46. (a) Bozell, J. J.; Hegedus, L. S. J. Org. Chem. 1981, 46, 2561-2563.
47. (b) Kasahara, A.; Izumi, T.; Murakami, S.; Yanai, H.; Takatori, M. Bull. Chem. Soc. Jpn. 1986, 59, 927-928.
48. Edmondson, S. D.; Mastracchio, A.; Parmee, E. R. Org. Lett. 2000, 2, 1109-1112.
49. Latham, E. J.; Stanforth, S. P. J. Chem. Soc., Perkin Trans. 1 1997, 2059-2063.
50. Chen, C.-Y.; Lieberman, D. R.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1997, 62, 2676-2677.
51. Nazaré, M.; Schneider, C.; Lindenschmidt, A.; Will, D. W. Angew. Chem., Int. Ed. 2004, 43, 4526-4528.
52. Lachnace, N.; April, M.; Joly, M.-A. Synthesis 2005, 2571-2577.
53. Part of this work has been published as a preliminary communication: Jia, Y.; Zhu, J. Synlett 2005, 2469-2472.
54. Shinohara, T.; Deng, H.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc 2005, 127, 7334-7336.
55. (a) Allen, M. C.; Brundish, D. E.; Wade, R. J. Chem. Soc., Perkin Trans. 1 1980, 1928-1932.
56. (b) Konda-Yamada, Y.; Okada, C.; Yoshida, K.; Umeda, Y.; Arima, S.; Sato, N.; Kai, T.; Takayanagi, H.; Harigaya, Y. Tetrahedron 2002, 58, 7851-7861.
57. (a) Lee, M.; Phillips, R. S. Bioorg. Med. Chem. Lett. 1992, 2, 1563-1564.
58. (b) Kaiser, M.; Groll, M.; Renner, C.; Huber, R.; Moroder, L. Angew. Chem., Int. Ed. 2002, 41, 780-783.
59. (a) Hino, T.; Taniguchi, M. J. Am. Chem. Soc. 1978, 100, 5564-5565.
60. (b) Taniguchi, M.; Anjiki, T.; Nakagawa, M.; Hino, T. Chem. Pharm. Bull. 1984, 32, 2544-2554.
61. (a) Yokoyama, Y.; Matsumoto, T.; Murakami, Y. J. Org. Chem. 1995, 60, 1486-1487.
62. (b) Wang, W.; Xiong, C.; Yang, J.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 7717-7719.
63. Liu, R.; Zhang, P.; Gan, T.; Cook, J. M. J. Org. Chem. 1997, 62, 7447-7456.
64. Berthelot, A.; Piguel, S.; Le Dour, G.; Vidal, J. J. Org. Chem. 2003, 68, 9835-9838.
65. (a) Elder, A. M.; Rich, D. H. Org. Lett. 1999, 1, 1443-1446.
66. (b) Drury, W. J., III; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 11006-11007.
67. Gorohovsky, S.; Meir, S.; Shkoulev, V.; Byk, G.; Gelleman, G. Synlett 2003, 1411-1414.
68. (a) Ma, C.; Liu, X.; Li, X.; Flippen-Anderson, J.; Yu, S.; Cook, J. M. J. Org. Chem. 2001, 66, 4525-4542.
69. (b) Li, X.; Yin, W.; Srirama Sarma, P. V. V.; Zhao, H.; Ma, J.; Cook, J. M. Tetrahedron Lett. 2004, 45, 8569-8573.
70. (c) Castle, S. L.; Srikanth, G. S. C. Org. Lett. 2003, 5, 3611-3614.
71. Zhu, X.; Ganesan, A. J. Org. Chem. 2002, 67, 2705-2708.
72. (b) Bandini, M.; Melloni, A.; Umani-Ronchi, A. Org. Lett. 2004, 6, 3199-3202.
73. (c) Kimura, M.; Futamata, M.; Mukai, R.; Tamaru, Y. J. Am. Chem. Soc. 2005, 127, 4592-4593.
74. (d) Grimster, N. P.; Gauntlett, C.; Godfrey, C. R. A.; Gaunt, M. J. Angew. Chem., Int. Ed. 2005, 44, 3125-3129.
75. For recent examples of Fisher indole syntheses, see: (a) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251-10263.
76. (b) Ref 31.
77. (c) Campos, K. R.; Woo, J. C. S.; Lee, S.; Tillyer, R. D. Org. Lett. 2004, 6, 79-82.
78. (d) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1996, 37, 4869-4872.
79. Bold, G.; Steiner, H.; Moesch, L.; Walliser, B. Helv. Chim. Acta 1990, 73, 405-410.
80. (a) Baran, P. S.; Guerrero, C. A.; Ambhaikar, N. B.; Hafensteiner, B. D. Angew. Chem., Int. Ed. 2005, 44, 606-609.
81. (b) Baran, P. S.; Hafensteiner, B. D.; Ambhaikar, N. B.; Guerrero, C. A.; Gallagher, J. D. J. Am. Chem. Soc. 2006, 128, 8678-8693.
82. (a) Kokotos, G.; Padron, J. M.; Martin, T.; Gibbons, W. A.; Martin, V. S. J. Org. Chem. 1998, 63, 3741-3744.
83. (b) Padron, J. M.; Kokotos, G.; Martin, T.; Markidis, T.; Gibbons, W. A.; Martin, V. S. Tetrahedron: Asymmetry 1998, 9, 3381-3394.
84. For halide effects on metal-catalyzed transformations, see: Fagnou, K.; Lautens, M. Angew. Chem., Int. Ed. 2002, 41, 26-47.
85. Yadav, J. S.; Reddy, B. V. S.; Reddy, K. S. Synlett 2002, 468-470.
86. For a review of palladium-catalyzed cross-coupling reactions of aryl chlorides, see: (a) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176-4211.
87. For recent examples, see: (b) Kudo, N.; Perseghini, M.; Fu, G. C. Angew. Chem., Int. Ed. 2006, 45, 1282-1284.
88. (c) Billingsley, K. L.; Anderson, K. W.; Buchwald, S. L. Angew. Chem., Int. Ed. 2006, 45, 3484-3488.
89. (d) For a recent example of catalytic direct arylation of aryl chloride, see: Campeau, L.-C.; Parisien, M.; Jean, A.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 581-591.
90. (a) Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L.; Pace, P. Synlett 1997, 1363-1366.
91. (b) Lane, B. S.; Brown, M. A.; Sames, D. J. Am. Chem. Soc. 2005, 127, 8050-8057.
92. For a review of stereoselective Friedel - Crafts alkylation reaction, see: Bandini, M.; Melloni, A.; Umani-Ronchi, A. Angew. Chem., Int. Ed. 2004, 43, 550-556.
93. For metal-catalyzed additions of indoles to α,β-unsaturated systems, see: (a) Evans, D. A.; Scheidt, K. A.; Fandrick, K. R.; Lam, H. W.; Wu, J. J. Am. Chem. Soc. 2003, 125, 10780-10781.
94. (b) Zhou, J.; Ye, M.-C.; Huang, Z.-Z.; Tang, Y. J. Org. Chem. 2004, 69, 1309-1320.
95. (c) Palomo, C.; Oiarbide, M.; Kardak, B. G.; García, J. M.; Linden, A. J. Am. Chem. Soc. 2005, 127, 4154-4155.
96. (d) Evans, D. A.; Fandrick, K. R.; Song, H.-J. J. Am. Chem. Soc. 2005, 127, 8942-8943.
97. For organo-catalyzed additions of indoles to α,β-unsaturated systems, see: (a) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172-1173.
98. (b) King, H. D.; Meng, Z.; Denhart, D.; Mattson, R.; Kimura, R.; Wu, D.; Gao, Q.; Macor, J. E. Org. Lett. 2005, 7, 3437-3440.
99. (c) Herrera, R. P.; Sgarzani, V.; Bernardi, L.; Ricci, A. Angew. Chem., Int. Ed. 2005, 44, 6576-6579.
100. (a) Oikawa, Y.; Hirasawa, H.; Yonemitsu, O. Tetrahedron Lett. 1978, 1759-1762.
101. (b) Dardennes, E.; Kovacs-Kulyassa, A.; Renzetti, A.; Sapi, J.; Laronze, J.-Y. Tetrahedron Lett. 2003, 44, 221-223.
102. (a) Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617-620.
103. (b) Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719-2724.
104. (c) Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295-4298.
105. (d) Littke, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 6343-6348.
106. (a) Huang, X.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 6653-6655.
107. (b) Nguyen, H. N.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 11818-11819.
108. (c) Willis, M. C.; Brace, G. N.; Holmes, I. P. Synthesis 2005, 3229-3234.
109. For N-arylation of ortho-chloroaniline, see: Bedford, R. B.; Cazin, C. S. J. Chem. Commun. 2002, 2310-2311.
110. For synthesis of indole via arylation of ortho-halonitroarenes followed by reductive cyclization, see: Rutherford, J. L.; Rainka, M. P.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 15168-15169.
111. Wang, W.; Xiong, C.; Zhang, J.; Hruby, V. J. Tetrahedron 2002, 58, 3101-3110.
112. Banwell, M. G.; Kelly, B. D.; Kokas, O. J.; Lupton, D. W. Org. Lett. 2003, 5, 2497-2500.
113. (a) Russell, G. A.; Yao, C.-F.; Tashtoush, H. I.; Russell, J. E.; Dedolph, D. F. J. Org. Chem. 1991, 56, 663-669.
114. (b) Fürstner, A.; Jumbam, D. N. Tetrahedron 1992, 48, 5991-6010.
115. Campos, K. R.; Woo, J. C. S.; Lee, S.; Tillyer, R. D. Org. Lett. 2004, 6, 79-82.