Rhodium(I)-catalyzed synthesis of indoles: Amino-claisen rearrangement of N-propargylanilines

Journal of Organic Chemistry

Volumn 74, Issue 4, 2009, Pages 1517-1524

  Saito, Akio ^a   Oda, Shoko ^a   Fukaya, Haruhiko ^b   Hanzawa, Yuji ^a  

^a SHOWA PHARMACEUTICAL UNIVERSITY   (Japan)

^b TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE CATALYSTS; CATALYTIC SYSTEMS; CATALYZED REACTIONS; CATALYZED SYNTHESIS; CLAISEN REARRANGEMENTS; FACILE PREPARATIONS; HEXAFLUOROISOPROPYL ALCOHOLS; IN-SITU; INDOLE COMPOUNDS; ONE-POT SYNTHESIS; PROPARGYL BROMIDES; RHODIUMS (I); X-RAY CRYSTALLOGRAPHIC ANALYSIS;

AMINATION; AMINES; ETHERS; ORGANIC POLYMERS; RHODIUM COMPOUNDS;

RHODIUM;

ANILINE DERIVATIVE; BROMIDE; COPPER; INDOLE DERIVATIVE; PALLADIUM; RHODIUM; TRANSITION ELEMENT;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CLAISEN REARRANGEMENT; CYCLIZATION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ANILINE COMPOUNDS; BROMIDES; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; INDOLES; ORGANOMETALLIC COMPOUNDS; PROPANOLS; RHODIUM;

EID: 64349090667     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8022523     Document Type: Article

References (100)

1. (a) Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127.
2. (b) Widenhoefer, R. A. Acc. Chem. Res. 2002, 35, 905.
3. (c) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901.
4. (a) Mckay, M. J.; Carroll, A. R.; Quinn, R. J.; Hooper, J. N. A. J. Nat. Prod. 2002, 65, 595.
5. (b) Verpoorte, R. Alkaloids 1998, 397.
6. (c) Sundberg, R. J. Prog. Heterocycl. Chem. 1989, 1, 111.
7. (d) Soxon, J. E. Nat. Prod. Rep. 1986, 3, 357.
8. (e) Toyota, M.; Ihara, M. Vat. Prod. Rep. 1998, 15, 327.
9. (f) Joule, J. A. In Science of Synthesis; Thomas, E. J., Ed.; Thieme: Stuttgart, 2000; Vol. 10, p 261.
10. (g) Hibino, S.; Chosi, T. Nat. Prod. Rep. 2002, 19, 148.
11. (h) Gribble, G. W. J. Chem. Soc, Perkin Trans. 1 2000, 1045.
12. (i) Faulkner, D. J. Nat. Prod. Rep. 1999, 16, 155.
13. (j) Lounasmaa, M.; Tolvanen, A. Nat. Prod. Rep. 2000, 17, 175.
14. For recent reviews, see: (a) Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875.
15. (b) Patil, S.; Buolamwini, J. K. Curr. Org. Chem. 2006, 3, 477.
16. (c) Patil, S.; Patil, R. Curr. Org. Chem. 2007, 4, 201.
17. (a) Kusama, H.; Takaya, J.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 11592.
18. (b) Kusama, H.; Suzuki, Y.; Takaya, J.; Iwasawa, N. Org. Lett. 2006, 8, 895.
19. (c) Terada, Y.; Arisawa, M.; Nishida, A. Angew. Chem., Int. Ed. 2004, 43, 4063.
20. (a) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671, and references cited therein.
21. (b) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Parisi, L. M. J. Org. Chem. 2005, 70, 6213.
22. (c) Yasuhara, A.; Takeda, Y.; Suzuki, N.; Sakamoto, T. Chem. Pharm. Bull. 2002, 50, 235.
23. (d) Shen, Z.; Lu, X. Tetrahedron 2006, 62, 10896.
24. (e) Takeda, A.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 5662.
25. (f) Cacchi, S.; Fabrizi, G.; Pace, P. J. Org. Chem. 1998, 29, 1001.
26. For examples of Cu(I)-mediated or catalyzed reactions, see: (a) Castro, C. E.; Stephens, R. D. J. Org. Chem. 1963, 28, 2163.
27. (b) Villemin, D.; Goussu, D. Heterocycles 1989, 29, 1255.
28. (c) Kamijo, S.; Sasaki, Y.; Yamamoto, Y. Tetrahedron Lett. 2004, 45, 35.
29. (d) Batsm, C. G.; Saejueng, P.; Murphy, J. M.; Venkataraman, D. Org. Lett. 2002, 4, 4727.
30. (e) Cacchi, S.; Fabrizi, G.; Parisi, L. M. Org. Lett. 2003, 5, 3843.
31. For an example of a Cu(II)-catalyzed reaction, see: (a) Hiroya, K.; Itoh, S.; Sakamoto, T. J. Org. Chem. 2004, 69, 1126.
32. (b) For an example of a Ag- catalyzed reaction, see: Van Esseveldt, B. C. J.; van Delft, F. L.; Smits, J. M. M.; de Gelder, R.; Schoemaker, H. E.; Rutjes, F. P. Z. J. T. Adv. Synth. Catal. 2004, 346, 823.
33. (d) For an example of an Ir-catalyzed reaction, see: Li, X.; Chianese, A. R.; Vogel, T.; Crabtree, R. H. Org. Lett. 2005, 7, 5437.
34. (e) For an example of In-catalyzed reaction, see: Sakai, N.; Annaka, K.; Konakahara, T. Org. Lett. 2004, 6, 1527.
35. (a) Shimada, T.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 10546. See:
36. (b) Nakamura, I.; Mizushima, Y.; Yamamoto, Y. J. Am. Chem. Soc. 2005, 127, 15022.
37. Alfonsi, M.; Arcadi, A.; Aschi, M.; Bianchi, G.; Marinelli, F. J. Org. Chem. 2005, 70, 2265.
38. Recently, Rh(I)-catalyzed cyclization of o-alkynylaniline derivatives has been reported through a vinylidenerhodium intermediate. Trost, B. M.; McClory, A. Angew. Chem., Int. Ed. 2007, 46,1.
39. (a) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689.
40. (b) Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652.
41. (c) Larock, R. C. Pure. Appl. Chem. 1999, 71, 1435. See:
42. (d) Shen, M.; Li, G.; Lu, B. Z.; Hossain, A.; Roschanger, F.; Farina, V.; Senanayake, C. H. Org. Lett. 2004, 6, 4129.
43. (a) Chen, C.-Y.; Lieberman, D. R.; Larsen, R. D.; Reamer, R. A.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1994, 35, 6981.
44. (b) Yu, J.; Wearing, X. Z.; Cook, M. J. Org. Chem. 2005, 70, 3963.
45. (c) Parmentier, J.-G.; Poissonnet, G.; Goldstein, S. Heterocycles. 2002, 56, 465.
46. (d) Gathergood, N.; Scammells, P. J. Org. Lett. 2003, 5, 921.
47. For a review, see: Nevado, C.; Echavarren, A. M. Synthesis 2005, 167.
48. For recent intramolecular hydroarylation type reaction, see: (a) Chatani, N.; Inoue, H.; Ikeda, T.; Murai, S. J. Org. Chem. 2000, 65, 4913.
49. (b) Martin- Matute, B.; Cardenas, D. J.; Echavarren, A. M. Angew. Chem., Int. Ed. 2001, 40, 4754.
50. (c) Furstner, A.; Mamane, V. J. Org. Chem. 2002, 67, 6264.
51. (d) Thalj, R. K.; Ahrendt, K. A.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 9692.
52. (e) Hashmi, A. S. K.; Blanco, M. C.; Kurpejovic, E.; Frey, W.; Bats, J. W. Adv. Synth. Catal. 2006, 348, 709.
53. (a) Pastine, S. J.; Youn, S. W.; Sames, D. Org. Lett. 2003, 5, 1055.
54. (b) Pastine, S. J.; Youn, S. W.; Sames, D. Tetrahedron 2003, 59, 8859.
55. (c) Nishizawa, M.; Takao, H.; Yadav, V. K.; Imagawa, H.; Sugihara, T. Org. Lett. 2003, 5, 4563.
56. (d) Martin-Matute, B.; Nevado, C.; Cardenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2003, 125, 5757.
57. (e) Nieto-Oberhuber, C.; Mmioz, M. P.; Bmiuel, E.; Nevado, C.; Cardenas, D. J.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 2402.
58. (a) Magnus, P.; Mitchell, I. S. Tetrahedron Lett. 1998, 39, 4595.
59. (b) Erzhanov, K. B.; Kolkhosova, S. S.; Sadykov, T. Zh. Org. Khim. 1989, 25, 1729.
60. For a review, see: (a) Lutz, R. P. Chem. Rev. 1984, 84, 205.
61. (b) Castro, A. M. M. Chem. Rev. 2004, 104, 2939.
62. (c) Kouznetsov, V. V. J. Heterocycl. Chem. 2005, 42, 39.
63. Related monograph: Krause, N. A. Hashmi, S. K. Modern Allene Chemistry; Wiley-VCH: Weinheim, 2004; Vol. 1, pp 1-50.
64. (a) Scheurer, H.; Zsindely, J.; Schmid, H. Helv. Chim. Acta 1973, 56, 478.
65. (b) Majumdar, K. C.; Bhattacharyya, T. Tetrahedron Lett. 2001, 42, 4231.
66. (c) Brønsted acid-promoted rearrangement: Barmettler, P.; Hansen, H.-J. Helv. Chim. Acta 1990, 73, 1515.
67. (a) Dillard, R. D.; Pavey, D. E.; Benslay, D. N. J. Med. Chem. 1973, 16, 253.
68. (b) Barmettler, P.; Hansen, H.-J.; Dillard, R. D. J. Org. Chem. 1962, 27, 4713.
69. (c) Holman, M. A.; Williamson, N. M.; Ward, A. D. Aust. J. Chem. 2005, 58, 368.
70. The aromatic Claisen rearrangements of propargyl ether derivatives usually afford 6-membered ring fused arenes; see: (a) Koch-Pomeranz, U.; Hansen, H.-J.; Schmid, H. Helv. Chim. Acta 1973, 56, 2981.
71. (b) Olsson, L. I.; Claesson, A. Synthesis 1979, 743.
72. (c) See also: Ishii, H.; Ishikawa, T.; Takeda, S.; Ueki, S.; Suzuki, M.; Harayama, T. Chem. Pharm. Bull. 1992, 38, 1775.
73. Saito, A.; Kanno, A.; Hanzawa, Y. Angew. Chem., Int. Ed. 2007, 46, 3931.
74. Our previous reports about Rh(I)-catalyzed reactions in fluorinated alcohol: (a) Saito, A.; Ono, T.; Hanzawa, Y. J. Org. Chem. 2006, 71, 6437.
75. (b) Saito, A.; Ono, T.; Takahashi, A.; Taguchi, T.; Hanzawa, Y. Tetrahedron. Lett. 2006, 47, 891.
76. (c) Saito, A.; Hironaga, M.; Oda, S.; Hanzawa, Y. Tetrahedron Lett. 2007, 45, 6852.
77. 2CDOD, hydrogen at the 2-position of HFIP did not take part in the hydrogenation reaction. See: (a) Fujita, K.; Kitatsuji, C.; Furukawa, S.; Yamaguchi, R. Tetrahedron Lett. 2004, 45, 3215.
78. (a) Schoneboom, J. C.; Groetsch, S.; Christl, M.; Engels, B. Chem. -Eur. J. 2003, 9, 4641.
79. (b) Forrest, T. P.; Dauphinee, G. A.; Deraniyagala, S. A. Can. J. Chem. 1985, 63, 412.
80. (c) See also ref 17a.
81. 3 (2a: 37%).
82. It is instructive to note that a small amount of 9a has already been generated under MeMgBr/Cu(I) conditions.
83. (a) Jardine, F. H. Polyhedron 1982, 1, 569, and references cited therein.
84. (b) Trzeciak, A. M.; Olejnik, Z.; Ziolkowski, J. J.; Lis, T. Inorg. Chim. Acta 2003, 350, 339.
85. Donghi, D.; Beringhelli, T.; D'Alfonso, G.; Mondini, M. Chem.-Eur. J. 2006, 12, 1016.
86. Hayashi, Y.; Komiya, S.; Yamamoto, T.; Yamamoto, A. Chem. Lett. 1984, 1363.
87. CCDC 696799 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
88. 3. Each route i, ii, or iii has been previously reported; see: (a) Kung, C.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 1674.
89. (b) Booth, B. L.; Casey, G. C.; Haszeldine, R. N. J. Organomet. Chem. Soc. 1982, 224, 197.
90. Kegley, S. E.; Schaverien, C. J.; Freudenberger, J. H.; Bergman, R. G.; Nolan, S. P.; Hoff, C. D. J. Am. Chem. Soc. 1987, 109, 6563.
91. Pd-fluorinated alkoxide complex with 1 equiv of fluorinated alcohol led to the formation of analogue hydrogen-bonded species; see: (a) Kim, Y.-J.; Osakada, K.; Takenaka, A.; Yamamoto, A. J. Am. Chem. Soc. 1990, 112, 1096.
92. (b) Kapteijn, G. M.; Spee, M. P. R.; Grove, D. M.; Kooijman, H.; Spek, A.; van Koten, G. Organometallics 1996, 15, 1405.
93. (a) Heaton, B. T.; Jacob, C.; Sampanthar, J. T. J. Chem. Soc., Dalton Trans. 1998, 1403.
94. (b) Bassetti, M.; Capone, A.; Mastrofrancesco, L.; Salamone, M. Organometallics 2003, 22, 2535.
95. (c) Tsuruta, H.; Imamoto, T.; Yamaguchi, K.; Gridnev, I. D. Tetrahedron Lett. 2005, 46, 2879.
96. (d) Ezhova, M. B.; Patrick, B. O.; James, B. R. Organometallics 2005, 24, 3753.
97. The proton of MeOH coordinated with the Rh-complex appeared at 3.74 ppm, which agreed with signal b of 25 and HFIP mixture. See ref 32b.
98. It is impossible for us to use 8a for NMR study since the rapid formation of 9a disturbed the NMR study.
99. See, refs 17a, 20, and 21.
100. Swenton, J. S.; Shih, C.; Chen, C. P.; Chou, C. T. J. Org. Chem. 1990, 55, 2019.