Coupling reactions of alkynylsilanes mediated by a Cu(I) salt: Novel syntheses of conjugate diynes and disubstituted ethynes

Journal of Organic Chemistry

Volumn 65, Issue 6, 2000, Pages 1780-1787

  Nishihara, Yasushi ^a   Ikegashira, Kazutaka ^a   Hirabayashi, Kazunori ^a   Ando, Jun Ichi ^a   Mori, Atsunori ^a   Hiyama, Tamejiro ^a,b  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE DERIVATIVE; ACETYLENE; ALKYNE; COPPER CHLORIDE; SILANE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0034708636     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991686k     Document Type: Article

References (107)

1. Schmidt, H.-W.; Guo, D. Makromol. Chem. 1988, 189, 2029.
2. (a) Holmes, A. B.; Jennings-White, C. L. D.; Kendrick, D. A. J. Chem. Soc., Chem. Commun. 1983, 415.
3. (b) Crombie, L.; Hobbs, A. J. W.; Horsham, M. A. Tetrahedron Lett. 1987, 28, 4875.
4. (c) Holmes, A. B.; Tabor, A. B.; Baker, R. J. Chem. Soc., Perkin Trans. 1 1991, 3307.
5. (d) Hoye, T. R.; Chanson, P. R. Tetrahedron Lett. 1993, 34, 5043.
6. Stüts, A. Angew, Chem., Int. Ed. Engl. 1987, 26, 320.
7. For general reviews on coupling reactions between sp carbon center, see: Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 3, pp 551-561.
8. (a) Schlubach, H. H.; Franzen, V. J. Liebigs Ann. Chem. Soc. 1951, 116.
9. (b) Black, H. K; Horn, D. H. S.; Weedon, B. C. L. J. Chem. Soc. 1954, 1704.
10. (a) Hay, A. S. J. Org. Chem. 1962, 27, 3320.
11. (b) Jones, G. E.; Kendrick, D. A.; Holmes, A. B. Org. Synth. 1987, 65, 52.
12. (c) Valentí, E.; Pericàs, M. A.; Serratosa, F. J. Am. Chem. Soc. 1990, 112, 7401.
13. (a) Rossi, R.; Carpita, A.; Bigelli, C. Tetrahedron Lett. 1985, 26, 523.
14. (b) Liu, Q.; Burton, D. J. Tetrahedron Lett. 1997, 38, 4371.
15. Whitesides G. M.; Casey, C. P. J. Am. Chem. Soc. 1966, 88, 4541.
16. (a) Nicolaou, K. C.; Zipkin, R. E.; Dolle, R. E.; Harris, B. D. J. Am. Chem. Soc. 1984, 106, 3548.
17. (b) Just, G.; O'Connor, B. Tetrahedron Lett. 1988, 29, 753.
18. (a) Ames, D. E.; Brohi, M. I. J. Chem. Soc., Perkin Trans. 1 1980, 1384.
19. (b) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Chem. Pharm. Bull. 1985, 33, 626.
20. (c) Tilley, J. W.; Zawoiski, S. J. Org. Chem. 1988, 53, 386.
21. (d) Taylor, E. C.; Ray, P. S. J. Org. Chem. 1988, 53, 35.
22. (e) Chapdelaine, M. J.; Warwick, P. J.; Shaw, A. J. Org. Chem. 1989, 54, 1218.
23. (a) Fouquey, C.; Lehn, J.-M.; Malthête, J. J. Chem. Soc., Chem. Commun. 1987, 1424.
24. (b) Chang, J. Y.; Baik, J. H.; Le, C. B.; Han, M. J. J. Am. Chem. Soc. 1997, 119, 3197.
25. (c) Kitamura, T.; Lee, C. H.; Taniguchi, Y.; Fujiwara, Y.; Matsumoto, M.; Sano, Y. J. Am. Chem. Soc. 1997, 119, 619.
26. (a) Goldfinger, M. B.; Crawford, K. B.; Swager, T. M. J. Phys. Chem. 1991, 95, 10643.
27. (b) Kanis, D. R.; Ratner, M. A.; Marks, T. J. Chem. Rev. 1994, 94, 195.
28. (a) Bunten, K. A.; Kakkar, A. K. Macromolecules 1996, 29, 2885.
29. (b) Takagi, M.; Kizu, K.; Miyazaki, Y.; Maruyama, T.; Kubota, K.; Yamamoto, T. Chem. Lett. 1993, 913.
30. (c) Ley, K. D.; Whittle, C. E.; Bartberger, M. D.; Schanze, K. S. J. Am. Chem. Soc. 1997, 119, 3423.
31. Xu, Z.; Kaha, M.; Walker, K. L.; Wilkins, C. L.; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 4537.
32. (a) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467.
33. (b) Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N. Synthesis 1980, 627.
34. (a) de Meijere, A.; Kozhushkov, S.; Haumann, T.; Boese, R.; Puls, C.; Cooney, M. J.; Scott, L. T. Chem. Eur. J. 1995, 1, 124.
35. (b) Haley, M. M.; Bell, M. L.; Brand, S. C.; Kimball, D. B.; Pak, J. J.; Wan, W. B. Tetrahedron Lett. 1997, 38, 7483.
36. (c) Babudri, F.; Fiandanese, V.; Marchese, G.; Punzi, A. J. Organomet. Chem. 1998, 566, 251.
37. (a) Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1988, 53, 918.
38. (b) Hatanaka, Y.; Matsui, K.; Hiyama, T. Tetrahedron Lett. 1989, 30, 2403.
39. (c) Hiyama T. Metal-Catalyzed Cross-Coupling Reactions. In Organo-silicon Compounds in Cross-Coupling Reactions; Diederich F., Stang P. J., Eds.; Wiley-VCH: 1998; Chapter 10, pp 421-454.
40. (d) Mowery, M. E.; DeShong, P. J. Org. Chem. 1999, 64, 1684.
41. (e) Denmark, S. E.; Choi, J. Y. J. Am. Chem. Soc. 1999, 121, 5821.
42. For preliminary commnications, see: (a) Ikegashira, K.; Nishihara, Y.; Hirabayashi, K.; Mori, A.; Hiyama, T. Chem. Commun. 1997, 1039. (b) Nishihara, Y.; Ikegashira, K.; Mori, A.; Hiyama, T. Chem. Lett. 1997, 1233. (c) Nishihara, Y.; Ikegashira, K.; Mori, A.; Hiyama, T. Tetrahedron Lett. 1998, 39, 4075.
43. For preliminary commnications, see: (a) Ikegashira, K.; Nishihara, Y.; Hirabayashi, K.; Mori, A.; Hiyama, T. Chem. Commun. 1997, 1039. (b) Nishihara, Y.; Ikegashira, K.; Mori, A.; Hiyama, T. Chem. Lett. 1997, 1233. (c) Nishihara, Y.; Ikegashira, K.; Mori, A.; Hiyama, T. Tetrahedron Lett. 1998, 39, 4075.
44. For preliminary commnications, see: (a) Ikegashira, K.; Nishihara, Y.; Hirabayashi, K.; Mori, A.; Hiyama, T. Chem. Commun. 1997, 1039. (b) Nishihara, Y.; Ikegashira, K.; Mori, A.; Hiyama, T. Chem. Lett. 1997, 1233. (c) Nishihara, Y.; Ikegashira, K.; Mori, A.; Hiyama, T. Tetrahedron Lett. 1998, 39, 4075.
45. The use of triethylamine or pyridine barely effected the reaction of 1a with a stoichiometric amount of CuCl to yield 3a in 9% and 1%, respectively. No trace of 3a was obtained in acetonitrile, THF, or toluene.
46. Recently, papers suggesting of transmetalation from silicon to copper have appeared. See: (a) Kang, S.-K.; Kim, T.-H.; Pyun, S.-J. J. Chem. Soc., Perkin Trans. 1 1997, 797. (b) Ito, H.; Arimoto, K.; Sensui, H.-o.; Hosomi, A. Tetrahedron Lett. 1997, 38, 3977. (c) Pagenkopf, B. L.; Krüger, J.; Stojanovic, A.; Carreira, E. H. Angew. Chem., Int. Ed. 1998, 37, 3124. (d) Franz, A. K.; Woerpel, K. A. J. Am. Chem. Soc. 1999, 121, 949.
47. Recently, papers suggesting of transmetalation from silicon to copper have appeared. See: (a) Kang, S.-K.; Kim, T.-H.; Pyun, S.-J. J. Chem. Soc., Perkin Trans. 1 1997, 797. (b) Ito, H.; Arimoto, K.; Sensui, H.-o.; Hosomi, A. Tetrahedron Lett. 1997, 38, 3977. (c) Pagenkopf, B. L.; Krüger, J.; Stojanovic, A.; Carreira, E. H. Angew. Chem., Int. Ed. 1998, 37, 3124. (d) Franz, A. K.; Woerpel, K. A. J. Am. Chem. Soc. 1999, 121, 949.
48. Recently, papers suggesting of transmetalation from silicon to copper have appeared. See: (a) Kang, S.-K.; Kim, T.-H.; Pyun, S.-J. J. Chem. Soc., Perkin Trans. 1 1997, 797. (b) Ito, H.; Arimoto, K.; Sensui, H.-o.; Hosomi, A. Tetrahedron Lett. 1997, 38, 3977. (c) Pagenkopf, B. L.; Krüger, J.; Stojanovic, A.; Carreira, E. H. Angew. Chem., Int. Ed. 1998, 37, 3124. (d) Franz, A. K.; Woerpel, K. A. J. Am. Chem. Soc. 1999, 121, 949.
49. Recently, papers suggesting of transmetalation from silicon to copper have appeared. See: (a) Kang, S.-K.; Kim, T.-H.; Pyun, S.-J. J. Chem. Soc., Perkin Trans. 1 1997, 797. (b) Ito, H.; Arimoto, K.; Sensui, H.-o.; Hosomi, A. Tetrahedron Lett. 1997, 38, 3977. (c) Pagenkopf, B. L.; Krüger, J.; Stojanovic, A.; Carreira, E. H. Angew. Chem., Int. Ed. 1998, 37, 3124. (d) Franz, A. K.; Woerpel, K. A. J. Am. Chem. Soc. 1999, 121, 949.
50. The use of a polar solvent, DMF, is essential to promote the reaction. We consider that DMF would coordinate to an alkynylsilane to form the pentacoordinate but tetravalent species, which may behave as a pentavalent organosilicate that is formed by the addition of a fluoride ion to the organosilane and is known to be highly active to transmetalation.
51. For instance, the appropriate choice of 1 and 8 furnished cross-coupling products 11, 11b, and 11d in 97, >99, and >99% yields, respectively, whereas the unfavored combination (1c with 8b, 1c with 8f, and 1e with 8f) decreased the yields (30, 19, and 27%, respectively).
52. On the contrary, a triflate bearing an acetyl group at the orthoposition gave a trace amount of the cross-coupled product.
53. (a) Mitchell, M. B.; Wallbank, P. J. Tetrahedron Lett. 1991, 32, 2273.
54. (b) Portnoy, M.; Ben-David, Y.; Milstein, D. Organometallics 1993, 12, 4734.
55. (c) Grushin, V. V.; Alper, H. Chem. Rev. 1994, 94, 1047.
56. (d) Niecke, E.; Becker, F.; Nieger, M.; Stalke, D.; Schoeeller, W. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 1849.
57. (e) Gouda, K.-i.; Hagiwara, E.; Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1996, 61, 7232.
58. (f) Shen, W. Tetrahedron Lett. 1997, 38, 5575.
59. (g) Reddy, N. P.; Tanaka, M. Tetrahedon Lett. 1997, 38, 4807.
60. (h) Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10.
61. (i) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1999, 38, 2411.
62. (j) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64, 3804.
63. dppf = 1,1′-bis(diphenylphosphino)ferrocene, dppe = 1,2-bis-(diphenylphosphino)ethane, dppp = 1,3-bis(diphenylphosphino)propane, and dppb = 1,4-bis(diphenylphosphino)butane.
64. The palladium-catalyzed cross-coupling reaction of aryl triflates with terminal alkynes to give the corresponding Sonogahshira coupling products without CuI has been reported. See: Chen, Q.-Y.; Yang, Z.-Y. Tetrahedron Lett. 1986, 27, 1171.
65. (a) Stiegman, A. E.; Miskowski, V. M.; Perry, J. W.; Coulter, D. R. J. Am. Chem. Soc. 1987, 109, 5884.
66. (b) Graham, E. M.; Miskowski, V. M.; Perry, J. W.; Coulter, D. R.; Stiegman, A. E.; Schaefer, W. P.; Marsh, R. E. J. Am. Chem. Soc. 1989, 111, 8771.
67. (c) Stiegman, A. E.; Graham, E.; Perry, K. J.; Khundkar, L. R.; Cheng, L.-T.; Perry, J. W. J. Am. Chem. Soc. 1991, 113, 7658.
68. (a) Cadiot, P.; Chodkiewicz, W. C. R. Hebd. Seance Acad. Sci. 1955, 241, 1055.
69. (b) Chodkiewicz, W. Ann. Chim. Paris 1957, 2, 819.
70. Philippe, J. L.; Chodkiewicz, W.; Cadiot, P. Tetrahedron Lett. 1970, 1795.
71. Alami, M.; Ferri, F. Tetrahedron Lett. 1996, 37, 2763 and references therein.
72. Homo-coupling of aryl- and alkenylsilanes in the presence of a copper salt will be described in due course: Nishihara, Y.; Ikegashira, K.; Toriyama, F.; Mori, A.; Hiyama, T. Bull. Chem. Soc. Jpn., in press.
73. Chatt, J.; Mann, F. G. J. Chem. Soc. 1939, 1622.
74. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon Press: Oxford, 1988; p 322.
75. Campbell, I. B. The Sonogashira Cu-Pd-catalyzed alkyne coupling reaction. In Organocopper Reagents A Practical Approach; Taylor, R. J. K.. Ed.; Oxford University Press: Oxford, 1994; pp 217-235.
76. Benkeser, R. A.; Hickner, R. A. J. Am. Chem. Soc. 1958, 80, 5298.
77. Genet, J. P.; Balart, E.; Savinac, M. Synlett 1992, 715.
78. Soderquist, J. A.; Rane, A. M.; Mates, K.; Ramos, J. Tetrahedron Lett. 1995, 36, 6847.
79. Ashby, E. C.; Noding, S. A. J. Org. Chem. 1980, 45, 1035.
80. Uchida, K.; Utimoto, K.; Nozaki, H. J. Org. Chem. 1976, 41, 2215.
81. Hayami, H.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1984, 25, 4433.
82. Liu, Q.; Burton, D. J. Tetrahedron Lett. 1997, 38, 4371.
83. Galamb, V.; Gopal, M.; Alper, H. Organometallics 1983, 2, 801.
84. Akiyama, T.; Amino, M.; Saitou, T.; Utsunomiya, K.; Seki, K.; Ikoma, Y.; Kajitani, M.; Sugiyama, T.; Shimizu, K.; Sugimori, A. Bull. Chem. Soc. Jpn. 1998, 71, 2351.
85. Hubert, A. J. J. Chem. Soc. 1965, 6669.
86. Subramanian, L. R.; Hanack, M.; Chang, L. W. K.; Imhoff, M. A.; Schleyer, P. R.; Kurtz, W.; Stang, P. J.; Dueber, T. E. J. Org. Chem. 1976, 41, 4099.
87. Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478.
88. McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1980, 21, 4313.
89. Stang, P. J.; Anderson, A. G. J. Org. Chem. 1976, 41, 781.
90. Cabri, W.; Candiani, I.; Bedeschi, A.; Penco, S.; Santi, R. J. Org. Chem. 1992, 57, 1481.
91. Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033.
92. McMurry, J. E.; Mohanraj, S. Tetrahedron Lett. 1983, 24, 2723.
93. Keumi, T.; Saga, H.; Taniguchi, R.; Kitajima, H. Chem. Lett. 1977, 1099.
94. Perces, V.; Bae, J.-Y.; Zhao, M.; Hill, D. H. J. Org. Chem. 1995, 60, 176.
95. Stephens, R. D.; Castro, C. E. J. Org. Chem. 1963, 28, 3313.
96. Kiryu, T.; Ebisawa, M. Patent, JP 07188095 Heisei; Chem. Abstr. 1995, 123, 301658w.
97. Larrock, R. C.; Doty, M. J.; Cacchi, S. J. J. Org. Chem. 1993, 58, 4579.
98. Bresse, M. Patent, FR 2243023 750404; Chem. Abstr. 1975, 83, 171287s.
99. Zimmer, O.; Vollenberg, W.; Seipp, U.; Englberger, S.; Strohmann, W.; Haurand, M.; Bosman, B. J.; Schneider, J. Patent, EP 91-111487 910710; Chem. Abstr. 1992, 117, 26103v.
100. Rausch, M. D.; Tokas, E. F.; Mintz, E. A.; Clearfield, A.; Mangion, M.; Bernal, I. J. Organomet. Chem. 1979, 172, 109.
101. Agawa, T.; Miller, S. I. J. Am. Chem. Soc. 1961, 83, 449.
102. Yamanaka, H.; Shiraiwa, M.; Edo, K.; Sakamoto, T. Chem. Pharm. Bull. 1979, 27, 270.
103. Cassar, L. J. Organomet. Chem. 1975, 93, 253.
104. Hsu, C. S.; Tsay, K. T.; Chang, A. C.; Wang, S. R.; Wu, S. T. Liq. Cryst. 1995, 19, 409.
105. Beltrame, P. L.; Cattania, M. G.; Simonetta, M. J. Chem. Soc., Perkin Trans. 2 1973, 63.
106. Villieras, J.; Perriot, P.; Normant, J. F. Synthesis 1975, 458.
107. Nelson, D. J.; Blue, C. D.; Brown, H. C. J. Am. Chem. Soc. 1982, 104, 4913.