Recent advances in intramolecular alkyne cyclotrimerization and its applications

Current Organic Chemistry

Volumn 9, Issue 6, 2005, Pages 503-519

  Yamamoto, Yoshihiko ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; NATURAL PRODUCT; ORGANIC COMPOUND; TRANSITION ELEMENT;

CATALYST; CYCLIZATION; CYCLOTRIMERIZATION; REVIEW; SYNTHESIS;

EID: 17844363516     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272053544399     Document Type: Review

References (150)

1. (a) Shore, N. E. [2 + 2 + 2] Cycloadditions. In Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I.; Paquette, L. A., Eds.; Pergamon: Oxford, 1991, Vol. 5, pp. 1129-1162.
2. (b) Grotjahn, D.B. Transition Metal Alkyne Complexes: Transition Metal-catalyzed Cyclotrimerization. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G.; Hegedus, L. S., Eds.; Pergamon: Oxford, 1995; Vol. 12, pp. 741-770.
3. (c) Bönnemann, H.; Brijoux, W., Cyclomerization of Alkynes. In Transition Metals for Organic Synthesis; Beller, M.; Bolm, C., Eds.; Wiley: Weinheim, 1998; Vol 1, pp. 114-135.
4. (a) Wakatsuki, Y.; Kuramitsu, T.; Yamazaki, H. Tetrahedron Lett. 1974, 4549.
5. (b) Yamazaki, H.; Wakatsuki, Y. J. Organomet. Chem. 1977, 139, 157.
6. (a) Takahashi, T.; Kotora, M.; Xi, Z. J. Chem. Soc. Chem. Commun. 1995, 361.
7. (b) Takahashi, T.; Xi, Z.; Yamazaki, A.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 1998, 120, 1672.
8. (c) Takahashi, T.; Tsai, F.-Y.; Li, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 1999, 121, 11093.
9. (a) Suzuki, D.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2001, 123, 7925.
10. (b) Tanaka, R.; Nakano, Y.; Suzuki, D.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2002, 124, 9682.
11. (a) Müller, E.; Thomas, R.; Sauerbier, M.; Langer, E.; Streichfuss, D. Tetrahedron Lett. 1971, 521.
12. (b) Müller, E. Synthesis, 1974, 761, and references.
13. Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100 2901.
14. Reppe, W.; Schweckendiek, W. J. Justus Liebigs Ann. Chem. 1948, 560, 104.
15. (a) Lindner, E.; Jansen, R.-M.; Mayer, H. A.; Hiller, W.; Fawzi, R. Organometallics 1989, 8, 2355.
16. (b) Lindner, E.; Kühbauch, H. J. Organomet. Chem. 1991, 403, C9.
17. (c) Ren, C. Y.; Cheng, W. C.; Chan, W. C.; Yeung, C. H.; Lau, C. P. J. Mol. Catal. 1990, 59, L1.
18. (d) Bohanna, C.; Esteruelas, M. A.; Herrero, J.; López, A. M.; Oro, L. A. J. Organomet. Chem. 1995, 498, 199.
19. (e) Breschi, C.; Piparo, L.; Pertici, P.; Caporusso, A. M.; Vitulli, G. J. Organomet. Chem. 2000, 607, 57.
20. (a) Peters, J.-U.; Blechert, S. Chem. Commun. 1997 1983.
21. (b) Witulski, B.; Stengel, T.; Fernández-Hernández, J. M. Chem. Commun. 2000, 1965.
22. (c) Hoven, G. B.; Efskind, J.; RØmming, C.; Undheim, K. J. Org. Chem. 2002, 67, 2459.
23. (a) Yamamoto, Y.; Ogawa, R. Itoh, K. Chem. Commun. 2000, 549.
24. (b) Yamamoto, Y.; Arakawa, T.; Ogawa, R.; Itoh, K. J. Am. Chem. Soc. 2003, 125, 12143.
25. Yamamoto, Y.; Kinpara, K.; Saigoku, T.; Nishiyama, H.; Itoh, K. Org. Biomol. Chem. 2004, 2, 1287.
26. Yamamoto, Y.; Hata, K.; Arakawa, T.; Itoh, K. Chem. Commun. 2003, 1290.
27. (a) Müller, E.; Scheller, A.; Winter, W.; Wagner, F.; Meier, H. Chem.-Ztg. 1975, 99, 155.
28. (b) Hillard III, R. L.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1977, 99, 4058.
29. (c) McDonald, F. E.; Zhu, H. Y. H.; Holmquist, C. R. J. Am. Chem. Soc. 1995, 117, 6605.
30. Kirchner, K.; Calhorda, M. J.; Schmid, R.; Veiros, L. F. J. Am. Chem. Soc. 2003, 125, 11721.
31. Yamamoto, Y.; Ishii, J.; Nishiyama, H.; Itoh, K. J. Am. Chem. Soc. 2004, 126, 3712.
32. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95 2457.
33. (a) Yamazaki, H.; Hagihara, N. J. Organomet. Chem. 1966, 7, P22.
34. (b) Yamazaki, H.; Hagihara, N. J. Organomet. Chem. 1970, 21, 431.
35. Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1984, 23, 539.
36. Chouraqui, G.; Petit, M.; Aubert, C.; Malacria, M. Org. Lett. 2004, 6, 1519.
37. Slowinski, F.; Aubert, C.; Malacria, M. Adv. Synth. Catal. 2001, 343, 64.
38. Gandon, V.; Leca, D.; Aechtner, T.; Vollhardt, K. P. C.; Malacria, M.; Aubert, C. Org. Lett. 2004, 6, 3405.
39. (a) Green, J. R. Synlett 2001, 353-356.
40. (b) Mohamed, A. B.; Green, J. R. Chem. Commun. 2003 2936.
41. Sugihara, T.; Wakabayashi, A.; Nagai, Y.; Takao, H.; Imagawa, H.; Nishizawa, M. Chem. Commun. 2002, 576.
42. (a) Grigg, R.; Scott, R.; Stevenson, P. Tetrahedron Lett. 1982, 23, 2691.
43. (b) Grigg, R.; Scott, R.; Stevenson, P. J. Chem. Soc., Perkin Trans. 1 1988, 1357.
44. Grigg, R.; Savic, V.; Tambyrajah, V. Tetrahedron Lett. 2000, 41, 3003.
45. Grigg, R.; Sridharan, V.; Wang, J.; Xu, J. Tetrahedron 2000, 56, 8967.
46. Witulski, B.; Alayrac, C. Angew. Chem. Int. Ed. 2002 41, 3281.
47. Kinoshita, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 7784.
48. (a) Collman, J. P.; Kang, J. W.; Little, W. F.; Sullivan, M. F. Inorg. Chem. 1968, 7, 1298.
49. (b) Field, L. D.; Ward, A. J.; Turner, P. Aust. J. Chem. 1999, 52, 1085.
50. Partially intramolecular cyclotrimerizations with stoichiometric iridium complexes were reported, see: Müller, E.; Beissner, C. Chem.-Ztg. 1972, 96, 170.
51. Takeuchi, R.; Tanaka, S.; Nakaya, Y. Tetrahedron Lett. 2001, 42, 2991.
52. Later, the catalytic cyclotrimerization of ethynylbenzene were reported, see: Farnetti, E.; Marsich, N. J. Organomet. Chem. 2004, 689, 14.
53. Shibata, T.; Fujimoto, T.; Yokota, K.; Takagi, K. J. Am. Chem. Soc. 2004, 126, 8382.
54. After this report, similar asymmetric cyclotrimerizations of diynes and propargyl acetates by means of a Rh(I)(H8-binap) catalyst was also reported, see: Tanaka, K.; Nishida, G.; Wada, A.; Noguchi, K. Angew. Chem. Int. Ed. 2004, 43, 6510.
55. (a) Chiusoli, G. P.; Pallini, L.; Terenghi, G. Transition Met. Chem. 1983, 8, 189.
56. (b) Bhatarah, P.; Smith, E. H. J. Chem. Soc. Perkin Trans. 1 1990, 2603.
57. (c) Bhatarah, P.; Smith, E. H. J. Chem. Soc., Chem. Commun. 1991, 277.
58. (d) Bhatarah, P.; Smith, E. H. J. Chem. Soc. Perkin Trans. 1 1992, 2163.
59. (e) Duckworth, D. M.; Lee-Wong, S.; Slawin, A. M. Z.; Smith, E. H.; Williams, D. J. J. Chem. Soc. Perkin Trans. 1 1996, 815.
60. (f) Sato, Y.; Nishimata, T.; Mori, M. J. Org. Chem. 1994, 59, 6133.
61. (g) Sato, Y.; Nishimata, T.; Mori, M. Heterocycles 1997, 44, 443.
62. (h) Sato, Y.; Ohhashi, K.; Mori, M. Tetrahedron Lett. 1999, 40, 5231.
63. (a) Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988 88, 1047.
64. (b) Broene, R. D.; Buchwald, S. L. Science 1993, 261, 1696.
65. (c) Bennett, M. A.; Wenger, E. Chem. Ber./Recueil 1997, 130, 1029.
66. (a) Bennett, M. A.; Wenger, E. Organometallics 1995 14, 1267.
67. (b) Bennett, M. A.; Wenger, E. Organometallics 1996 15, 5536.
68. (c) Bennett, M. A.; Cobley, C. J.; Rae, A. D.; Wenger, E.; Willis, A. C. Organometallics 2000, 19, 1522.
69. (d) Bennett, M. A.; Macrregor, S. A.; Wenger, E. Helv. Chim. Acta 2001, 84, 3084.
70. (e) Edwards, A. J.; Willis, A. C.; Wenger, E. Organometallics 2002, 21, 1654.
71. (a) Peña, D.; Pérez, D.; Guitián, E.; Castedo, L. J. Am. Chem. Soc. 1999, 121, 5827-5828.
72. (b) Peña, D.; Pérez, D.; Guitián, E.; Castedo, L. Synlett 2000, 1061-1063.
73. (c) Peña, D.; Pérez, D.; Guitián, E.; Castedo, L. J. Org. Chem. 2000, 65, 6944-6950.
74. (d) Radhakrishnan, K. V.; Yoshikawa, E.; Yamamoto, Y. Tetrahedron Lett. 1999, 40, 7533-7535.
75. Peña, D.; Pérez, D.; Guitián, E.; Castedo, L. Eur. J. Org. Chem. 2003, 1238.
76. (a) Mosely, K.; Maitlis, P. M. Chem. Commun. 1971 1604.
77. (b) Mosely, K.; Maitlis, P. M. J. Chem. Soc., Dalton 1974, 169.
78. (a) Yamamoto, Y.; Nagata, A.; Itoh, K. Tetrahedron Lett. 1999, 40, 5035.
79. (b) Yamamoto, Y.; Nagata, A.; Arikawa, Y.; Tatsumi, K.; Itoh, K. Organometallics 2000, 19, 2403.
80. (c) Yamamoto, Y.; Nagata, A.; Nagata, H.; Ando, Y.; Arikawa, Y.; Tatsumi, K., Itoh, K. Chem. Eur. J. 2003, 9, 2469.
81. Pla-Quintana, A.; Roglans, A.; Torrent, A.; Moreno-Mañas, M.; Benet-Buchholz, J. Organometallics 2004, 23, 2762.
82. (a) Takahashi, T.; Kotora, M.; Xi, Z. J. Chem. Soc., Chem. Commun. 1995, 361.
83. (b) Takahashi, T.; Xi, Z.; Yamazaki, A.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 1998, 120, 1672.
84. (c) Takahashi, T.; Tsai, F.-Y.; Li, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 1999, 121, 11093.
85. (a) Negishi, E.; Takahashi, T. Synthesis 1988, 1.
86. (b) Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994 27, 124.
87. (a) Takahashi, T.; Hara, R.; Nishihara, Y.; Kotora, M. J. Am. Chem. Soc. 1996, 118, 5154.
88. (b) Takahashi, T.; Li, Y.; Stepnicka, P.; Kitamura, M.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 2002, 124 576.
89. (a) Suzuki, D.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2001, 123, 7925.
90. (b) Tanaka, R.; Nakano, Y.; Suzuki, D.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2002, 124, 9682.
91. (c) Hanazawa, T.; Suzuki, K.; Takayama, Y.; Sato, F. J. Org. Chem. 2003, 68, 4980.
92. For example, see: Nishida, M.; Shiga, H.; Mori, M. J. Org. Chem. 1998, 63, 8606.
93. Ozerov, O. V.; Patrick, B. O.; Ladipo, F. T. J. Am. Chem. Soc. 2000, 122, 6423.
94. (a) Funk, R. L.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1979, 101, 215.
95. (b) Funk, R. L.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1980, 102, 5253.
96. (c) Hillard III, R. L.; Parnell, C. A.; Vollhardt, K. P. C. Tetrahedron 1983, 39, 905.
97. Bradley, A.; Motherwell, W. B.; Ujjainwalla, F. Chem. Commun. 1999, 917.
98. Kingston, D. G. I. Chem. Commun. 2001, 867.
99. Petit, M.; Chouraqui, G.; Phansavath, P.; Aubert, C.; Malacria, M. Org. Lett. 2002, 4, 1027.
100. (a) Kalogerakis, A.; Groth, U. Org. Lett. 2003, 5, 843-844.
101. (b) Kalogerakis, A.; Groth, U. Synlett 2003, 18886.
102. (a) Neeson, S. J.; Stevenson, P. J. Tetrahedron Lett. 1988, 29, 813.
103. (b) Neeson, S. J.; Stevenson, P. J. Tetrahedron 1989 45, 6239.
104. Witulski, B.; Zimmermann, A.; Gowans, N. D. Chem. Commun. 2002, 2984.
105. (a) Funk, R. L.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1976, 98, 6755.
106. (b) Funk, R. L.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1980, 102, 5245.
107. Anderson, E. A.; Alexanian, E. J.; Sorensen, E. J. Angew. Chem. Int. Ed. 2004, 43, 1998.
108. Sato, Y.; Tamura, T.; Mori, M. Angew. Chem. Int. Ed. 2004, 43, 2436.
109. (a) Vollhardt, K. P. C. Pure Appl. Chem. 1993, 65, 153.
110. (b) Holms, D.; Kumaraswamy, S.; Matzger, A. J.; Vollhardt, K. P. C. Chem. Eur. J. 1999, 5, 3399.
111. (a) Eickmeier, C.; Holmes, D.; Junga, H.; Matzger, A. J.; Scherhag, F.; Shim, M.; Vollhardt, K. P. C. Angew. Chem. Int. Ed. 1999, 38, 800.
112. (b) Han, S.; Bond, A. D.; Disch, R. L.; Holmes, D.; Schulman, J. M.; Teal,, S. J.; Vollhardt, K. P. C.; Whitener, G. D. Angew. Chem. Int. Ed. 2002, 41, 3223.
113. (c) Han, S.; Anderson, D. R.; Bond, A. D.; Chu, H. V.; Disch, R. L.; Holmes, D.; Schulman, J. M.; Teat, S. J.; Vollhardt, K. P. C.; Whitener, G. D. Angew. Chem. Int. Ed. 2002, 41, 3227.
114. (d) Bruns, D.; Miura, H.; Vollhardt, K. P. C. Org. Lett. 2003, 5, 549.
115. Also, see: (e) Bong, D. T.-Y.; Gentric, L.; Holmes, D.; Matzger, A. J.; Scherhag, F.; Vollhardt, K. P. C. Chem. Commun. 2002, 278.
116. (f) Dosa, P. I.; Whiener, G. D.; Vollhardt, K. P. C. Org. Lett. 2002, 4, 2075.
117. (g) Bong, D. T.-Y.; Chan, E. W. L.; Diercks, R.; Dosa, P. I.; Haley, M. M.; Matzger, A. J.; Miljanic, O.S.; Vollhardt, K. P. C. Org. Lett. 2004, 13, 2249.
118. Teplý, F.; Stará, I. G.; Starý, I.; Kollárovič, A.; Šaman, D.; Vyskočil, S.; Fiedler, P. J. Org. Chem. 2003, 68, 5193.
119. McDonald, F. E.; Smolentsev, V. Org. Lett. 2002, 4, 745.
120. (a) Fletcher, J. T.; Therien, M. J. J. Am. Chem. Soc. 2000, 122, 12393.
121. (b) Fletcher, J. T.; Therien, M. J. J. Am. Chem. Soc. 2002, 124, 4298.
122. (c) Fletcher, J. T.; Therien, M. J. Inorg. Chem. 2002, 41, 331.
123. (a) Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Material Science; Togni, A.; Hayashi, T.; Eds.; VCH, Weinheim, 1995.
124. (a) Schlögl, K.; Soukup, H. Tetrahedron Lett. 1967, 1181.
125. (b) Schlögl, K.; Soukup, H. Monatsch. Chem. 1968 99, 927.
126. (c) Yasufuku, K.; Yamazaki, H. J. Organomet. Chem. 1977, 127, 197.
127. (d) Yasufuku, K.; Aoki, K.; Yamazaki, H. Inorg. Chem. 1977, 16, 624.
128. (e) Mamane, V.; Ledoux-Rak, I.; Deveau, S.; Zyss, J.; Riant O. Synthesis 2003, 455.
129. Dufková L.; Císařová, I.; Štepnička, P.; Kotora, M. Eur. J. Org. Chem. 2003, 2882.
130. Yamamoto, Y.; Kataoka, H.; Kinpara, K.; Nishiyama, H.; Itoh, K. Lett. Org. Chem. 2005, in press.
131. (a) Turek, P.; Kotora, M.; Hocek, M.; Císařová, I. Tetrahedron Lett. 2003, 44, 785.
132. (b) Turek, P.; Kotora, M.; Tišlerová, I.; Hocek, M.; Votruba, I.; Císařová, I. J. Org. Chem. 2004, 69 9224.
133. (a) Rohr, J.; Thiericke, R. Nat Prod. Rep. 1992, 103.
134. (b) Parker, K. A. Pure Appl. Chem. 1994, 66 2135.
135. (c) Kaelin, D. E., Jr.; Lopez, O. D.; Martin, S. F. J. Am. Chem. Soc. 2001, 123, 6937.
136. (d) Kaelin, D. E., Jr.; Sparks, S. M.; Plake, H. R.; Martin, S. F. J. Am. Chem. Soc. 2003, 125, 12994.
137. (e) Apsel, B.; Bender, J. A.; Escobar, M.; Kaelin, D. E., Jr.; Lopez, O. D.; Martin, S. F. Tetrahedron Lett. 2003, 44, 1075.
138. (f) Chen, C.-Li.; Martin, S. F. Org. Lett. 2004, 6, 3581.
139. McDonald, F. E.; Zhu, H. Y. H.; Holmquist, C. R. J. Am. Chem. Soc. 1995, 117, 6605.
140. Yamamoto, Y.; Saigoku, T.; Ohgai, T.; Nishiyama, H.; Itoh, K. Chem. Commun. 2004, 2702.
141. Recent reviews: (a) Belvisi, L.; Colombo, L.; Manzoni, L.; Potenza, D.; Scolastico, C. Synlett 2004, 1449.
142. (b) Kotha, S. Acc. Chem. Res. 2003, 36, 342.
143. (c) Undheim, K.; Efskind, J.; Hoven, G. B. Pure Appl. Chem. 2003, 75, 279.
144. (d) Dougherty, D. A. Curr. Opin. Chem. Biol. 2000 4, 645.
145. (e) Gibson, S. E.; Guillo, N.; Tozer, M. J. Tetrahedron 1999, 55, 585.
146. (a) Kotha, S.; Brahmachary, E. Tetrahedron Lett. 1997, 38, 3561.
147. (b) Kotha, S.; Brahmachary, E. Bioorg. Med. Chem. 2002, 10, 2291.
148. (c) Kotha, S.; Brahmachary, E. J. Organomet. Chem. 2004, 689, 158.
149. Kotha, S.; Mohanraja, K.; Durani, S. Chem. Commun. 2000, 1909.
150. Kotha, S.; Sreenivasachary, N. Bioorg. Med. Chem. Lett. 2000, 10, 1413.