Pd(II)-Catalyzed Oxidative Homo-Coupling of Aryl-Metal Compounds Using Acrylate Dibromide Derivatives as Effective Oxidants

Synlett

Volumn 1997, Issue 10, 1997, Pages 1199-1201

  Yamaguchi, Shigehiro ^a   Ohno, Shigeki ^a   Tamao, Kohei ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000679773     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-998     Document Type: Article

References (34)

1. Knight, D. W. In Comprehensive Organic Synthesis: Selectivity, Strategy and Efficiency in Modern Organic Chemistry: Trost, B. M. and Fleming, I. Eds.; Pergamon Press: Oxford, 1991; Vol. 3, pp.481.
2. Homo-coupling of arylstannanes catalyzed by Pd(II) complex: (a) Kanemoto, S.; Matsubara, S.; Oshima, K.; Utimoto, K.; Nozaki, H. Chem. Lett. 1987, 5. (b) Shinya, Y.; Takata, A.; Kawaguchi, K.; Kikukawa, K. 65th Annual Meetings of the Chemical Society of Japan, Tokyo, March 1993, IE441. (c) Farina, V.; Krishnan, B.; Marshall, D. R.; Roth, G. P. J. Org. Chem. 1993, 58, 5434. (d) Friesen, R. W.; Loo, R. W.; Sturino, C. F. Can. J. Chem. 1994, 72, 1262.
3. Homo-coupling of arylstannanes catalyzed by Pd(II) complex: (a) Kanemoto, S.; Matsubara, S.; Oshima, K.; Utimoto, K.; Nozaki, H. Chem. Lett. 1987, 5. (b) Shinya, Y.; Takata, A.; Kawaguchi, K.; Kikukawa, K. 65th Annual Meetings of the Chemical Society of Japan, Tokyo, March 1993, IE441. (c) Farina, V.; Krishnan, B.; Marshall, D. R.; Roth, G. P. J. Org. Chem. 1993, 58, 5434. (d) Friesen, R. W.; Loo, R. W.; Sturino, C. F. Can. J. Chem. 1994, 72, 1262.
4. Homo-coupling of arylstannanes catalyzed by Pd(II) complex: (a) Kanemoto, S.; Matsubara, S.; Oshima, K.; Utimoto, K.; Nozaki, H. Chem. Lett. 1987, 5. (b) Shinya, Y.; Takata, A.; Kawaguchi, K.; Kikukawa, K. 65th Annual Meetings of the Chemical Society of Japan, Tokyo, March 1993, IE441. (c) Farina, V.; Krishnan, B.; Marshall, D. R.; Roth, G. P. J. Org. Chem. 1993, 58, 5434. (d) Friesen, R. W.; Loo, R. W.; Sturino, C. F. Can. J. Chem. 1994, 72, 1262.
5. Homo-coupling of arylstannanes catalyzed by Pd(II) complex: (a) Kanemoto, S.; Matsubara, S.; Oshima, K.; Utimoto, K.; Nozaki, H. Chem. Lett. 1987, 5. (b) Shinya, Y.; Takata, A.; Kawaguchi, K.; Kikukawa, K. 65th Annual Meetings of the Chemical Society of Japan, Tokyo, March 1993, IE441. (c) Farina, V.; Krishnan, B.; Marshall, D. R.; Roth, G. P. J. Org. Chem. 1993, 58, 5434. (d) Friesen, R. W.; Loo, R. W.; Sturino, C. F. Can. J. Chem. 1994, 72, 1262.
6. Homo-coupling of areneboronic acids and their derivatives catalyzed by Pd(II) complex: (a) Rao. V. V. R.; Kumar, C. V.; Devaprabhakara, D. J. Organomet. Chem. 1979, 179, C7. (b) Song, Z. Z.; Wong, H. N. C. J. Org. Chem. 1994, 59, 33. (c) Ye, X.-S.; Wong, H. N. C. J. Org. Chem. 1997, 62, 1940 . Traces of homo-coupled products of areneboronic acids are frequently observed in the Suzuki-Miyaura coupling: (d) Gillman, T.; Weeber, T. Synlett 1994, 649. (e) Campi, E. M.; Jackson, W. R.; Marcuccio, S. M.; Naeslund, C. G. M. J. Chem. Soc., Chem. Commun. 1994, 2395. Recently, the mechanism for the self-coupling of areneboronic acids catalyzed by the Pd(0) complex has been reported: (f) Moreno-Manas, M.; Perez, M.; Pleixats, R. J. Org. Chem. 1996, 61, 2346.
7. Homo-coupling of areneboronic acids and their derivatives catalyzed by Pd(II) complex: (a) Rao. V. V. R.; Kumar, C. V.; Devaprabhakara, D. J. Organomet. Chem. 1979, 179, C7. (b) Song, Z. Z.; Wong, H. N. C. J. Org. Chem. 1994, 59, 33. (c) Ye, X.-S.; Wong, H. N. C. J. Org. Chem. 1997, 62, 1940 . Traces of homo-coupled products of areneboronic acids are frequently observed in the Suzuki-Miyaura coupling: (d) Gillman, T.; Weeber, T. Synlett 1994, 649. (e) Campi, E. M.; Jackson, W. R.; Marcuccio, S. M.; Naeslund, C. G. M. J. Chem. Soc., Chem. Commun. 1994, 2395. Recently, the mechanism for the self-coupling of areneboronic acids catalyzed by the Pd(0) complex has been reported: (f) Moreno-Manas, M.; Perez, M.; Pleixats, R. J. Org. Chem. 1996, 61, 2346.
8. Homo-coupling of areneboronic acids and their derivatives catalyzed by Pd(II) complex: (a) Rao. V. V. R.; Kumar, C. V.; Devaprabhakara, D. J. Organomet. Chem. 1979, 179, C7. (b) Song, Z. Z.; Wong, H. N. C. J. Org. Chem. 1994, 59, 33. (c) Ye, X.-S.; Wong, H. N. C. J. Org. Chem. 1997, 62, 1940 . Traces of homo-coupled products of areneboronic acids are frequently observed in the Suzuki-Miyaura coupling: (d) Gillman, T.; Weeber, T. Synlett 1994, 649. (e) Campi, E. M.; Jackson, W. R.; Marcuccio, S. M.; Naeslund, C. G. M. J. Chem. Soc., Chem. Commun. 1994, 2395. Recently, the mechanism for the self-coupling of areneboronic acids catalyzed by the Pd(0) complex has been reported: (f) Moreno-Manas, M.; Perez, M.; Pleixats, R. J. Org. Chem. 1996, 61, 2346.
9. Homo-coupling of areneboronic acids and their derivatives catalyzed by Pd(II) complex: (a) Rao. V. V. R.; Kumar, C. V.; Devaprabhakara, D. J. Organomet. Chem. 1979, 179, C7. (b) Song, Z. Z.; Wong, H. N. C. J. Org. Chem. 1994, 59, 33. (c) Ye, X.-S.; Wong, H. N. C. J. Org. Chem. 1997, 62, 1940 . Traces of homo-coupled products of areneboronic acids are frequently observed in the Suzuki-Miyaura coupling: (d) Gillman, T.; Weeber, T. Synlett 1994, 649. (e) Campi, E. M.; Jackson, W. R.; Marcuccio, S. M.; Naeslund, C. G. M. J. Chem. Soc., Chem. Commun. 1994, 2395. Recently, the mechanism for the self-coupling of areneboronic acids catalyzed by the Pd(0) complex has been reported: (f) Moreno-Manas, M.; Perez, M.; Pleixats, R. J. Org. Chem. 1996, 61, 2346.
10. Homo-coupling of areneboronic acids and their derivatives catalyzed by Pd(II) complex: (a) Rao. V. V. R.; Kumar, C. V.; Devaprabhakara, D. J. Organomet. Chem. 1979, 179, C7. (b) Song, Z. Z.; Wong, H. N. C. J. Org. Chem. 1994, 59, 33. (c) Ye, X.-S.; Wong, H. N. C. J. Org. Chem. 1997, 62, 1940 . Traces of homo-coupled products of areneboronic acids are frequently observed in the Suzuki-Miyaura coupling: (d) Gillman, T.; Weeber, T. Synlett 1994, 649. (e) Campi, E. M.; Jackson, W. R.; Marcuccio, S. M.; Naeslund, C. G. M. J. Chem. Soc., Chem. Commun. 1994, 2395. Recently, the mechanism for the self-coupling of areneboronic acids catalyzed by the Pd(0) complex has been reported: (f) Moreno-Manas, M.; Perez, M.; Pleixats, R. J. Org. Chem. 1996, 61, 2346.
11. Homo-coupling of areneboronic acids and their derivatives catalyzed by Pd(II) complex: (a) Rao. V. V. R.; Kumar, C. V.; Devaprabhakara, D. J. Organomet. Chem. 1979, 179, C7. (b) Song, Z. Z.; Wong, H. N. C. J. Org. Chem. 1994, 59, 33. (c) Ye, X.-S.; Wong, H. N. C. J. Org. Chem. 1997, 62, 1940 . Traces of homo-coupled products of areneboronic acids are frequently observed in the Suzuki-Miyaura coupling: (d) Gillman, T.; Weeber, T. Synlett 1994, 649. (e) Campi, E. M.; Jackson, W. R.; Marcuccio, S. M.; Naeslund, C. G. M. J. Chem. Soc., Chem. Commun. 1994, 2395. Recently, the mechanism for the self-coupling of areneboronic acids catalyzed by the Pd(0) complex has been reported: (f) Moreno-Manas, M.; Perez, M.; Pleixats, R. J. Org. Chem. 1996, 61, 2346.
12. Homo-coupling of arylhalosilanes catalyzed by Cu(I) complex: Kang, S.-K.; Kim, T.-H.; Pyun, S.-J. J. Chem. Soc., Perkin Trans. 1, 1997, 797.
13. 2 using ACDB derivatives: Akiba, K.-y.; Shimizu, A.; Ohnari, H.; Ohkata, K. Tetrahedron Lett. 1985, 26, 3211.
14. Korhonen, I. O. O.; Pitkanen, M.; Korvola, J. N. J. Tetrahedron 1982, 38, 2837.
15. f = 0.25; 64 mg, 0.37 mmol) was also isolated in 74% yield based on Ph-ACDB.
16. (a) Liebeskind, L. S.; Fengl, R. W. J Org. Chem. 1990, 55, 5359.
17. (b) Farina, K.; Kapadia, S.; Krishnan, B.; Wang, C.; Liebeskind, L. S. J. Org. Chem. 1994, 59, 5905.
18. Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585.
19. (a) Suzuki, A. Pure Appl. Chem. 1985, 57, 1749.
20. (b) Suzuki, A. Pure Appl. Chem. 1991, 63, 419.
21. (c) Suzuki, A. Pure Appl. Chem. 1994, 66, 213. For a recent review, see: Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
22. (c) Suzuki, A. Pure Appl. Chem. 1994, 66, 213. For a recent review, see: Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
23. f = 0.38; 109 mg, 0.60 mmol) in 81% yield. In this case, ethyl cinnamate was isolated in 97% yield (258 mg, 1.46 mmol) based on Ph-ACDB.
24. (a) Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1988, 53, 918.
25. (b) Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1989, 54, 268.
26. (c) Hatanaka, Y.; Matsui, K.; Hiyama, T. Tetrahedron Lett. 1989, 30, 2403.
27. (d) Hatanaka, Y.; Hiyama, T. J. Am. Chem. Soc. 1990, 112, 7793. For a review, see: Hatanaka, Y.; Hiyama. T. Synlett 1991, 845.
28. (d) Hatanaka, Y.; Hiyama, T. J. Am. Chem. Soc. 1990, 112, 7793. For a review, see: Hatanaka, Y.; Hiyama. T. Synlett 1991, 845.
29. 2Et is similarly formed as a side product.
30. 2-ACDB, 1.5 mol. amt.) only without the Pd(II) catalyst, the coupled product bitolyl was formed only in 15% GLC yield, although with the Pd(II) complex, the yield reached 79% isolated yield (Table 3, entry 11). This result implies that the Cu(I) salt indeed promotes the homo-coupling of arylhalosilanes under the present conditions but does not work as a catalyst.
31. Transmetalation from organosilicon compounds to Cu(I) salt: (a) Yoshida, J.-i.; Tamao, K.; Kakui, T.; Kumada, M. Tetrahedron Lett. 1979, 1141. (b) Ikegashira, K.; Nishihara, Y.; Hirabayashi, K.; Mori, A.: Hiyama, T. Chem. Commun. 1997, 1039. (c) Ito, H.; Sensui, H.-o.; Arimoto, K.; Miura, K.; Hosomi, A. Chem. Lett. 1997, 639.
32. Transmetalation from organosilicon compounds to Cu(I) salt: (a) Yoshida, J.-i.; Tamao, K.; Kakui, T.; Kumada, M. Tetrahedron Lett. 1979, 1141. (b) Ikegashira, K.; Nishihara, Y.; Hirabayashi, K.; Mori, A.: Hiyama, T. Chem. Commun. 1997, 1039. (c) Ito, H.; Sensui, H.-o.; Arimoto, K.; Miura, K.; Hosomi, A. Chem. Lett. 1997, 639.
33. Transmetalation from organosilicon compounds to Cu(I) salt: (a) Yoshida, J.-i.; Tamao, K.; Kakui, T.; Kumada, M. Tetrahedron Lett. 1979, 1141. (b) Ikegashira, K.; Nishihara, Y.; Hirabayashi, K.; Mori, A.: Hiyama, T. Chem. Commun. 1997, 1039. (c) Ito, H.; Sensui, H.-o.; Arimoto, K.; Miura, K.; Hosomi, A. Chem. Lett. 1997, 639.
34. 1H NMR and GLC of the reaction mixture.