Gold(I)-catalyzed cyclizations of 1,6-enynes: Alkoxycyclizations and exol endo skeletal rearrangements

Chemistry - A European Journal

Volumn 12, Issue 6, 2006, Pages 1677-1693

  Nieto Oberhuber, Cristina ^a,b   Muñoz, M Paz ^b   López, Salomé ^a   Jiménez Núñez, Eloísa ^a,b   Nevado, Cristina ^b   Herrero Gómez, Elena ^a   Raducan, Mihai ^a   Echavarren, Antonio M ^a,b  

^a INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

^b UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

Alkynes; Cyclization; Gold; Iron; Rearrangement

Indexed keywords

CATALYST ACTIVITY; COMPLEXATION; GOLD; IRON; MERCURY (METAL); PALLADIUM; RHODIUM;

ALKYNES; CYCLIZATION; REARRANGEMENT;

ORGANIC COMPOUNDS;

EID: 32944481296     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200501088     Document Type: Article

References (103)

1. Reviews: a) G. C. Lloyd-Jones, Org, Biomol. Chem. 2003, 1, 215-236;
2. b) C. Aubert, O. Buisine, M. Malacria, Chem. Rev. 2002, 102, 813-834;
3. c) S. T. Diver, A. Giessert, J. Chem. Res. 2004, 104, 1317-1382;
4. d) A. M. Echavarren, M. Méndez, M. P. Muñoz, C. Nevado, B. Martín-Matute, C. Nieto-Oberhuber, D. J. Cárdenas, Pure Appl. Chem. 2004, 76, 453-463;
5. e) A. M. Echavarren, C. Nevado, Chem. Soc. Rev. 2004, 33, 431-436;
6. f) L. Añorbe, G. Domfnguez, J. Pérez-Castells, Chem. Eur. J. 2004, 10, 4938-4943;
7. g) C. Bruneau, Angew. Chem. 2005, 117, 2380-2386;
8. Angew, Chem. Int. Ed. 2005, 44, 2328-2334.
9. a) M. Méndez, M. P. Muñoz, A. M. Echavarren, J. Am. Chem. Soc. 2000, 122, 11549-11550;
10. b) M. Méndez, M. P. Muñoz, C. Nevado, D. J. Cárdenas, A. M. Echavarren, J. Am. Chem. Soc. 2001, 123, 10511-10520;
11. c) M. P. Muñoz, M. Méndez, C. Nevado, D. J. Cárdenas, A. M. Echavarren, Synthesis 2003, 2898-2902;
12. d) M. P. .Muñoz, J. Adrio, J. C. Carretero, A. M. Echavarren, Organometallics 2005, 24, 1293-1300.
13. a) C. Nevado, D. J. Cárdenas, A. M. Echavarren, Chem. Eur. J. 2003, 9, 2627-2635;
14. b) C. Nevado, C. Ferrer, A. M. Echavarren, Org. Lett. 2004, 6, 3191-3194.
15. a) B. M. Trost, F. D. Toste, J. Am. Chem. Soc. 2000, 122, 714-715;
16. b) P. Cao, B. Wang, X. Zhang, J Am. Chem. Soc. 2000, 122, 6490-6491.
17. a) N. Chatani, T. Morimoto, T. Muto, S. Murai, J. Am. Chem. Soc. 1994, 116, 6049-6050;
18. b) N. Chatani, N. Furukawa, H. Sakurai, S. Murai, Organometallics 1996, 15, 901-903;
19. c) N. Chatani, H. Inoue, T. Ikeda, S. Murai, J. Org. Chem. 2000, 05, 4913-4918.
20. a) E. Soriano, P. Ballesteros, J. Marco-Contelles, J. Org. Chem. 2004, 69, 8018-8023;
21. b) R.-X. He, M. Li, X.-Y. Li, J. Mol. Struct. 2005, 777, 21-32.
22. Hydroxycyclization catalyzed by mercuric triflate: M. Nishizawa, V. K. Yadav, M. Skwarczynski, H. Takao, H. Imagawa, T. Sugihara, Org. Lett. 2003, 5, 1609-1611.
23. C. Nevado, L. Charruault, V. Michelet, C. Nieto-Oberhuber, M. P. Muñoz, M. Méndez, M.-N. Rager, J.-P. Genêt, A. M. Echavarren, Eur. J. Org. Chem. 2003, 706-713.
24. J. Blum, H. Herr-Kraft, Y. Badrieh, J. Org. Chem. 1995, 60, 5567-5569.
25. a) A. Fürstner, H. Szillat, F. Stelzer, J. Am. Chem. Soc. 2000, 122, 6785-6786;
26. b) A. Fürstner, F. Stelzer, H. Szillat, J. Am. Chem. Soc. 2001, 123, 11863-11869.
27. S. Oi, I. Tsukamoto, S. Miyano, Y. Inoue, Organometallics 2001, 20, 3704-3709.
28. C. Nieto-Oberhuber, S. López, M. P. Muñoz, D. J. Cárdenas, E. Buñuel, C. Nevado, A.M. Echavarren, Angew. Chem. 2005, 117, 6302-6304;
29. Angew. Chem. Int. Ed. 2005, 44, 6146-6148.
30. a) B. M. Trost, G. J. Tanoury, J. Am. Chem. Soc. 1988, 110, 1636-1638;
31. b) B. M. Trost, M. K. Trost, Tetrahedron Lett. 1991, 32, 3647-3650;
32. c) B. M. Trost, M. Yanai, K. Hoogsteed, J. Am. Chem. Soc. 1993, 115, 5294-5295;
33. d) N. Chatani, H. Inoue, T. Kotsuma, S. Murai, J. Am. Chem. Soc. 2002, 124, 10294-10295;
34. e) F. Marion, J. Coulomb, C. Courillon, L. Fensterbank, M. Malacria, Org. Lett. 2004, 6, 1509-1511;
35. f) G. B. Bajracharya, I. Nakamura, Y. Yamamoto, J. Org. Chem. 2005, 70, 892-897.
36. C. Nieto-Oberhuber, S. López, A.M. Echavarren, J. Am. Chem. Soc. 2005, 127, 6178-6179.
37. A. Fürstner, P. W. Davies, T. Gress, J. Am. Chem. Soc. 2005, 727, 8244-8245.
38. C. Nieto-Oberhuber, M. P. Muñoz, E. Buñuel, C. Nevado, D.J. Cárdenas, A. M. Echavarren, Angew. Chem. 2004, 116, 2456-2460;
39. Angew. Chem. Int. Ed. 2004, 43, 2402-2406.
40. 1 catalysts; a) V. Mamane, T. Gress, H. Krause, A. Fürstner, J. Am. Chem. Soc. 2004, 126, 8654-8655;
41. b) M. R. Luzung, J. P. Markham, F.D. Toste, J. Am. Chem. Soc. 2004, 126, 10858-10859;
42. c) L. Zhang, S.A. Kozmin, J. Am. Chem. Soc. 2004, 726, 11806-11807;
43. d) L. Zhang, S. A. Kozmin, J. Am. Chem. Soc. 2005, 727, 6962-6963;
44. 1 catalysts; X. Shi, D. J. Gorin, F. D. Toste, J. Am. Chem. Soc. 2005, 727, 5802-5803.
45. C. Nieto-Oberhuber, S. López, M. P. Mufloz, E. Jiménez-Núñez, E. Bufluel, D. J. Cárdenas, A. M. Echavarren, Chem. Eur. J. 2006, 12, 1694-1702.
46. a) C. Fernández-Rivas, M. Méndez, A.M. Echavarren, J. Am. Chem. Soc. 2000, 122, 1221-1222;
47. b) C. Fernández-Rivas, M. Méndez, C. Nieto-Oberhuber, A. M. Echavarren, J. Org. Chem. 2002, 67, 5197-5201.
48. E. R. Stricter, D. G. Blackmond, S. L. Buchwald, J. Am. Chem. Soc. 2003, 125, 13978-13980.
49. a) S. D. Walker, T.E. Border, J. R. Martinelli, S. L. Buchwald, Angew. Chem. 2004, 116, 1907-1912;
50. Angew. Chem. Int. Ed. 2004, 43, 1871-1876;
51. b) S. Kaye, J. M. Fox, F. A. Hicks, S. L. Buchwald, Adv. Synth. Catal. 2001, 343, 789-794.
52. 3)Cl]; A. K. Al-Sa'ady, C. A. McAuliffe, R. V. Parish, J. A. Sandeank, Inorg. Synth. 1985, 23, 191-194.
53. a) B. Bovio, A. Burini, B. R. Pietroni, J. Organomet. Chem. 1993, 452, 287-291;
54. b) X. Hu, I. Castro-Rodriguez, K. Olsen, K. Meyer, Organometallics 2004, 23, 755-764, and references therein;
55. c) S. Singh, S. S. Kumar, V. Jancik, H. W. Roesky, H.-G. Schmidt, M. Noltemeyer, Eur. J. Inorg. Chem. 2005, 3057-3062.
56. P. de Fremont, N. M. Scott, E. D. Stevens, S. P. Nolan, Organometallics 2005, 24, 2411 -2418.
57. a) M. Preisenberger, A. Schier, H. Schmidbaur, J. Chem. Soc. Dalton Trans. 1999, 1645-1650;
58. b) K. A. Porter, A. Schier, H. Schmidbaur, Organometallics 2003, 22, 4922-4927.
59. Hydroarylation of alkynes catalyzed by [Au(PPh3)Cl] and silver salts: M. T. Reetz, K. Sommer, Eur. J. Org, Chem. 2003, 3485-3496.
60. I: a) J. H. Teles, S. Brode, M. Chabanas, Angew. Chem. 1998, 110, 1475-1478;
61. Angew. Chem. Int. Ed. 1998, 37, 1415-1418;
62. b) E. Mizushima, K. Sato, T. Hayashi, M. Tanaka, Angew. Chem. 1998, 110, 4745-4747;
63. Angew. Chem. Int. Ed. 2002, 41, 4563-4565.
64. B. M. Trost, J. Dumas, Tetrahedron Lett. 1993, 34, 19-22.
65. B.M. Trost, L. Zhi, K. Imi, Tetrahedron Lett. 1994, 35, 1361-1364.
66. For other examples of palladium-catalyzed endo-cyclizations proceeding by intramolecular insertion; see: S. Brown, S. Clarkson, R. Grigg, V. Sridharan, Tetrahedron Lett. 1993, 34, 157-160.
67. a) T. Kitamura, Y. Sato, M. Mori, Adv. Synth. Catal. 2002, 34, 344, 678-693;
68. b) M. Mori, J. Mol. Catal. A 2004, 213, 73-79.
69. H. Kim, C. Lee, J. Am. Chem. Soc. 2005, 127, 10180-10181.
70. 3Cl] can now be mechanistically reinterpreted as taken place via vinylidenes (Cf. ref. [32]): R. Grigg, P. Stevenson, T. Worakun, Tetrahedron 1988, 44, 4967-4972.
71. S. Yamazaki, K. Yamada, K. Yamamoto, Org. Biomol. Chem. 2004, 2, 257-264.
72. A. J. Pearson, R. A. Dubbert, Organometallics 1994, 13, 1656-1661.
73. K. Mikami, M. Hatano, Proc. Natl Acad. Sci. USA 2004, 101, 5767-5769.
74. Y. Yamamoto, S. Kuwabara, Y. Ando, H. Nagata, H. Nishiyama, K. Itoh, J. Org. Chem. 2004, 69, 6697-6705.
75. a)R. Hoffmann, Angew. Chem. 1982, 94, 725-739;
76. Angew. Chem. Int. Ed. Engl. 1982, 21, 711-724;
77. b) K.P. Hall, D.M.P. Mingos, Prog. Inorg. Chem. 1984, 32, 237-325.
78. B. M. Trost, R. Braslau, Tetrahedron Lett. 1988, 29, 1231-1234.
79. S.-I. Ikeda, H. Miyashita, M. Taniguchi, H. Kondo, M. Okano, Y. Sato, K. Odashima, J. Am. Chem. Soc. 2002, 124, 12060-12061.
80. T. Kataoka, H. Yoshimatsu, Y. Noda, T. Sato, H. Shimizu, M. Hori, J. Chem. Soc. Perkin Trans, 1 1987, 121-129.
81. B. M. Trost, M. Lautens, C. Chan, D. J. Jebaratnam, T. Mueller, J. Am. Chem. Soc. 1991, 113, 636-644.
82. B. M. Trost, K. Burgess, J. Chem. Soc. Chem. Commun. 1985, 1084-1086.
83. B. M. Trost, G. J. Tanoury, J. Am. Chem. Soc. 1987, 109, 4753-4755.
84. N. Jeong, Y. K. Chung, B. Y. Lee, S. H. Lee, S. E. Yoo, Synlett 1991, 204-206.
85. M. E. Krafft, L. V. R. Bonaga, J. A. Wright, C. Hirosawa, J. Org. Chem. 2002, 67, 1233-1246.
86. B. L. Pagenkopf, D. B. Belanger, D. J. R. O'Mahony, T. Livinghouse, Synthesis 2000, 1009-1019.
87. M. Ishizaki, K. Iwahara, Y. Niimi, H. Satoh, O. Hoshino, Tetrahedron 2001, 57, 2729-2738.
88. W. Oppolzer, A. Fürstner, Helv. Chim. Acta 1993, 76, 2329-2337.
89. A. M. Castaño, M. Ruano, A. M. Echavarren, Tetrahedron Lett. 1996, 57, 6591-6594.
90. T. R. Hoye, J. A. Suriano, Organometallics 1992, 11, 2044-2050.
91. Diethyl ester: Ref. [5a].
92. H.-Y. Lee, H. Y. Kim, H. Tae, B. G. Kim, J. Lee, Org. Lett. 2003, 5, 3439-3442.
93. C.-W. Lee, K. S. Oh, K. S. Kim, K. H. Ahn, Org. Lett. 2000, 2, 1213-1216.
94. S.-K. Kang, B.-S. Ko, D.M. Lee, Tetrahedron Lett. 2002, 43, 6693-6696.
95. B. M. Trost, D. C. Lee, F. Rise, Tetrahedron Lett. 1989, 30, 651-654.
96. M. Kimura, Y. Horino, R. Mukai, S. Tanaka, Y. Tamaru, J. Am. Chem. Soc. 2001, 123, 10401-10402.
97. T. E. Muller, J. C. Green, D. M. P. Mingos, C. M. McPartlin, C. Whittingham, D. J. Williams, T. M. Woodroffe, J. Organomet. Chem. 1998, 551, 313-330.
98. V. P. W. Böhm, T. Weskamp, C. W. K. Gstöttmayr, W. A. Herrmann, Angew. Chem. 2000, 112, 1672-1674;
99. Angew. Chem. Int. Ed. 2000, 39, 1602-1604.
100. M. G. Gardiner, W. A. Herrmann, C.-P. Reisinger, J. Schwarz, M. Spiegler, J. Organomet. Chem. 1999, 572, 239-247.
101. a)H.M.J. Wang, I.J.B. Lin, Organometallics 1998, 17, 972-975;
102. b) H. M. J. Wang, C. Y. L. Chen I. J. B. Lin, Organometallics 1999, 18, 1216-1223.
103. Synthesis of N',N'-dimethylimidazolium iodide : C. G. Overberger, J. C. Salamone, S. Yaroslavsky, J. Org. Chem. 1965, 30, 3580.