Atom transfer cyclization catalyzed by InCl3 via halogen activation

Organic Letters

Volumn 8, Issue 6, 2006, Pages 1045-1048

  Cook, Gregory R ^a   Hayashi, Ryuji ^a  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; HALOGENATED HYDROCARBON; INDIUM; INDIUM CHLORIDE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

ALKYNES; CATALYSIS; CYCLIZATION; HYDROCARBONS, HALOGENATED; INDIUM; MOLECULAR STRUCTURE;

EID: 33646440725     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052802a     Document Type: Article

References (83)

1. For recent reviews, see: (a) Matyjaszewski, K.; Miller, P. J.; Fossum, E.; Nakagawa, Y. Appl. Organomet. Chem. 1998, 12, 667.
2. (b) Delaude, L.; Demonceau, A.; Noels, A. F. Top. Organomet. Chem. 2004, 11, 155.
3. (c) Clark, A. J. Chem. Soc. Rev. 2002, 31, 1.
4. (d) Byers, J. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: New York, 2001; Vol. 1, pp 72-89.
5. (e) Yet, L. Tetrahedron 1999, 55, 9349.
6. (f) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 4, pp 779-831.
7. Pd: (a) Ma, S.; Lu, X. J. Organomet. Chem. 1993, 447, 305.
8. (b) Zhu, G.; Lu, X. J. Org. Chem. 1995, 60, 1087.
9. (c) Holzapfel, C. W.; Marais, L. Tetrahedron Lett. 1998, 39, 2179.
10. (d) Holzapfel, C. W.; Marais, L.; Toerien, F. Tetrahedron 1999, 55, 3467.
11. (e) Intermolecular Pd-catalyzed alkyne allylation: Thadani, A. N.; Rawal, V. H. Org. Lett. 2002, 4, 4317.
12. Rh is known to do enyne cyclization with concomitant halide migration: Tong, X.; Li, D.; Zhang, Z.; Zhang, X. J. Am. Chem. Soc. 2004, 126, 7601.
13. Miura, K.; Fujisawa, N.; Hosomi, A. J. Org. Chem. 2004, 69, 2427.
14. Reviews: (a) Araki, S.; Tsunehisa, H. In Main Group Metals in Organic Synthesis; Yamamoto, H., Oshima, K., Eds.; Wiley: New York, 2004; Vol. 1, pp 323-386.
15. (b) Nair, V.; Ros, S.; JaYan, C. N.; Pillai, B. S. Tetrahedron 2004, 60, 1959.
16. (c) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149.
17. (d) Ranu, B. C. Eur. J. Org. Chem. 2000, 2347.
18. (e) Pae, A. N.; Cho, Y. S. Curr. Org. Chem. 2002, 6, 715.
19. (a) Araki, S.; Imai, A.; Shimizu, K.; Butsugan, Y. Tetrahedron Lett. 1992, 33, 2581.
20. (b) Ranu, B. C.; Majee, A. Chem. Commun. 1997, 1225.
21. (c) Fujiwara, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2318.
22. (d) Fujiwara, N.; Yamamoto, Y. J. Org. Chem. 1999, 64, 4095.
23. (e) Klaps, E.; Schmid, W. J. Org. Chem. 1999, 64, 7537.
24. (f) Salter, M. M.; Sardo-Inffiri, S. Synlett 2002, 2068.
25. For examples of other carboindation reactions, see: (a) Capps, S. M.; Lloyd-Jones, G. C.; Murray, M.; Peakman, T. M.; Walsh, K. E. Tetrahedron Lett. 1998, 39, 2853.
26. (b) Höppe, H. A.; Lloyd-Jones, G. C.; Murray, M.; Peakman, T. M.; Walsh, K. E. Angew. Chem., Int. Ed. Engl. 1998, 37, 1545.
27. (c) Araki, S.; Nakano, H.; Subburaj, K.; Hirashita, T.; Shibutani, K.; Yamamura, H.; Kawai, M.; Butsugan, Y. Tetrahedron Lett. 1998, 39, 6327.
28. (d) Araki, S.; Horie, T.; Kato, M.; Hirashita, T.; Yamamura, H.; Kawai, M. Tetrahedron Lett. 1999, 40, 2331.
29. (e) Araki, S.; Kamei, T.; Igarshi, Y.; Hirashita, T.; Yamamura, H.; Kawai, M. Tetrahedron Lett. 1999, 40, 7999.
30. (f) Lim, H. J.; Keum, G.; Kang, S. B.; Kim, Y. Tetrahedron Lett. 1999, 40, 1547.
31. (g) Araki, S.; Shiraki, G.; Tanaka, T.; Nakano, H.; Subburaj, K.; Hirashita, T.; Yamamuru, H.; Kawai, M. Chem.-Eur. J. 2001, 7, 2784.
32. (a) Moody, C. J.; Pitts, M. R. Synlett 1998, 1028.
33. (b) Ranu, B. C.; Guchhait, S. K.; Sarkar, A. Chem. Commun. 1998, 2113.
34. (c) Ranu, B. C.; Dutta, P.; Sarkar, A. J. Chem. Soc., Perkin Trans. 1 1999, 1139.
35. (d) Reddy, G. V.; Rao, G. V.; Iyengar, D. S. Tetrahedron Lett. 1999, 40, 3937.
36. (e) Inoue, K.; Yasuda, M.; Shibata, I.; Baba, A. Tetrahedron Lett. 2000, 41, 113.
37. (f) Barman, D. C.; Thakur, A. J.; Prajapati, D.; Sandhu, J. S. Synlett 2001, 515.
38. (g) Ranu, B. C.; Dutta, J.; Guchhait, S. K. Org. Lett. 2001, 3, 2603.
39. (h) Ranu, B. C.; Samanta, S.; Guchhait, S. K. J. Org. Chem. 2001, 66, 4102.
40. (i) Ranu, B. C.; Dutta, J.; Guchhait, S. K. J. Org. Chem. 2001, 66, 5624.
41. (j) Ranu, B. C.; Banerjee, S.; Das, A. Tetrahedron Lett. 2004, 45, 8579.
42. (a) Araki, S.; Butsugan, Y. Bull. Chem. Soc. Jpn. 1991, 64, 727.
43. (b) Araki, S.; Shimizu, T.; Jebar, P. S.; Jin, J.; Butsugan, Y. J. Org. Chem. 1991, 56, 2538.
44. (c) Ranu, B. C.; Dutta, P.; Sarkar, A. Tetrahedron Lett. 1998, 39, 9557.
45. Jeevanandam, A.; Ling, Y.-C. Tetrahedron Lett. 2001, 42, 4361.
46. (a) Hayashi, N.; Shibata, I.; Baba, A. Org. Lett. 2005, 7, 3093.
47. (b) Hirashita, T.; Tanaka, J.; Hayashi, A.; Araki, S. Tetrahedron Lett. 2005, 46, 289.
48. (c) Takami, K.; Usugi, S.-I.; Yorimitsu, H.; Oshima, K. Synthesis 2005, 824.
49. (d) Hayashi, N.; Shibatta, I.; Baba, A. Org. Lett. 2004, 6, 4981.
50. (e) Takami, K.; Yorimitsu, H.; Oshima, K. Org. Lett. 2004, 6, 4555.
51. (f) Miyabe, H.; Ueda, M.; Nishimura, A.; Naito, T. Tetrahedron 2004, 60, 4227.
52. (g) Yanada, R.; Obika, S.; Nishimori, N.; Yamauchi, M.; Takemoto, Y. Tetrahedron Lett. 2004, 45, 2331.
53. (h) Miyabe, H.; Naito, T. Org. Biomol. Chem. 2004, 2, 1267.
54. (i) Ueda, M.; Miyabe, H.; Nishimura, A.; Miyata, O.; Takemoto, Y.; Naito, T. Org. Lett. 2003, 5, 3835.
55. (j) Miyabe, H.; Ueda, M.; Nishimura, A. Naito, T. Org. Lett. 2002, 4, 131.
56. (k) Takami, K.; Yorimitsu, H.; Oshima, K. Org. Lett. 2002, 4, 2993.
57. (l) Inoue, K.; Sawada, A.; Shibata, I.; Baba, A. J. Am. Chem. Soc. 2002, 124, 906.
58. (m) Jang, D. O.; Cho, D. H. Synlett 2002, 631.
59. (n) Yanada, R.; Nishimori, N.; Matsumura, A.; Fujii, N.; Takemoto, Y. Tetrahedron Lett. 2002, 43, 4585.
60. (o) Inoue, K.; Sawada, A.; Shibata, I.; Baba, A. Tetrahedron Lett. 2001, 42, 4661.
61. (a) Erickson, S.; Pararajasingham, K.; Cook, G. R. 217th ACS National Meeting, Anaheim, March 21-25, 1999; American Chemical Society: Washington, DC; ORGN-481.
62. (b) Cook, G. R.; Erickson, S.; Hvinden, M.; Reule, S. 219th ACS National Meeting, San Francisco, March 26-30, 2000; American Chemical Society: Washington, DC; ORGN-591.
63. (c) Cook, G. R.; Erickson, S.; Hvinden, M. 221st ACS National Meeting, San Diego, April 1-5, 2001; American Chemical Society: Washington, DC; ORGN-271.
64. Bhatti, N. H.; Salter, M. M. Tetrahedron Lett. 2004, 45, 8379.
65. The same product was obtained in low yield by treating the substrate with benzoyl peroxide in refluxing benzene.
66. A trace of 3 (<1%) was also detected.
67. Shibasaki has reported that In(III) salts activate alkynes for nucleophilic alkynylations. See: (a) Takita, R.; Yakura, K.; Ohshima, R.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 13760.
68. (b) Takita, R.; Fukuta, Y.; Tsuji, R.; Ohshima, T.; Shibasaki, M. Org. Lett. 2005, 7, 1363.
69. For recent examples of gold activation of alkynes, see: (a) Shi, X.; Gorin, D. J.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 5802.
70. (b) Zhang, L.; Kozmin, S. A. J. Am. Chem. Soc. 2005, 127, 6962.
71. (c) Sherry, B. D.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 15978.
72. (d) Füerstner, A.; Hannen, P. Chem. Commun. 2004, 2546.
73. (e) Steben, S. T.; Kennedy-Smith, J. J.; Toste, F. D. Angew. Chem., Int. Ed. 2004, 43, 5350.
74. (f) Zhang, L.; Kozmin, S. J. Am. Chem. Soc. 2004, 126, 11806.
75. (g) Mamane, V.; Gress, T.; Krause, H.; Fuerstner, A. J. Am. Chem. Soc. 2004, 126, 8654.
76. Hf Lewis acids catalyze the intramolecular allylsilation of alkynes via alkyne activation: Imamura, K.-I.; Yoshikawa, E.; Gevorgyan, V.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 5339.
77. Miller, A.; Moore, M. Tetrahedron Lett. 1980, 21, 577.
78. Only a few examples of halogen abstraction by vinyl cations from chlorinated solvents are known. (a) Johnson, W. S.; Ward, C. E.; Boots, S. G.; Gravestock, M. B.; Markezich, R. L.; McCarry, B. E.; Okorie, D. A.; Parry, R. J. J. Am. Chem. Soc. 1981, 103, 88.
79. (b) Balog, A.; Geib, S. V.; Curran, D. P. J. Org. Chem. 1995, 60, 345.
80. (c) Miranda, P. O.; Díaz, D. D.; Padrón, J. I.; Bermejo, J.; Martín, V. S. Org. Lett. 2003, 5, 1979.
81. (d) Sun, J.; Kozmin, S. A. J. Am. Chem. Soc. 2005, 127, 13512.
82. Overman has shown that nucleophiles accelerate the reaction of alkynes with cations: Overman, L. E.; Sharp, M. J. J. Am. Chem. Soc. 1988, 110, 612.
83. Poland, J. S.; Tuck, D. J. J. Organomet. Chem. 1972, 42, 315.