Copper(I) salt promoted homo-coupling reaction of organosilanes

Chemical Communications

Volumn , Issue 11, 1997, Pages 1039-1040

  Ikegashira, Kazutaka ^a   Nishihara, Yasushi ^a   Hirabayashi, Kazunori ^a   Mori, Atsunori ^a   Hiyama, Tamejiro ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002358128     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a701898c     Document Type: Article

References (21)

1. T. Hiyama and Y. Hatanaka, Pure Appl. Chem., 1994, 66, 1471; H. Matsuhashi, M. Kuroboshi, Y. Hatanaka and T. Hiyama, Tetrahedron Lett., 1994, 35, 6507; H. Matsuhashi, Y. Hatanaka, M. Kuroboshi and T. Hiyama, Heterocycles, 1996, 42, 375; H. Matsuhashi, S. Asai, K. Hirabayashi, Y. Hatanaka, A. Mori and T. Hiyama, Bull. Chem. Soc. Jpn., 1997, 70, 445; C. Chuit, R. J. P. Corriu, C. Reye and J. C. Young, Chem. Rev., 1993, 93, 1371; K. A. Horn, Chem. Rev., 1995, 95, 1371.
2. T. Hiyama and Y. Hatanaka, Pure Appl. Chem., 1994, 66, 1471; H. Matsuhashi, M. Kuroboshi, Y. Hatanaka and T. Hiyama, Tetrahedron Lett., 1994, 35, 6507; H. Matsuhashi, Y. Hatanaka, M. Kuroboshi and T. Hiyama, Heterocycles, 1996, 42, 375; H. Matsuhashi, S. Asai, K. Hirabayashi, Y. Hatanaka, A. Mori and T. Hiyama, Bull. Chem. Soc. Jpn., 1997, 70, 445; C. Chuit, R. J. P. Corriu, C. Reye and J. C. Young, Chem. Rev., 1993, 93, 1371; K. A. Horn, Chem. Rev., 1995, 95, 1371.
3. T. Hiyama and Y. Hatanaka, Pure Appl. Chem., 1994, 66, 1471; H. Matsuhashi, M. Kuroboshi, Y. Hatanaka and T. Hiyama, Tetrahedron Lett., 1994, 35, 6507; H. Matsuhashi, Y. Hatanaka, M. Kuroboshi and T. Hiyama, Heterocycles, 1996, 42, 375; H. Matsuhashi, S. Asai, K. Hirabayashi, Y. Hatanaka, A. Mori and T. Hiyama, Bull. Chem. Soc. Jpn., 1997, 70, 445; C. Chuit, R. J. P. Corriu, C. Reye and J. C. Young, Chem. Rev., 1993, 93, 1371; K. A. Horn, Chem. Rev., 1995, 95, 1371.
4. T. Hiyama and Y. Hatanaka, Pure Appl. Chem., 1994, 66, 1471; H. Matsuhashi, M. Kuroboshi, Y. Hatanaka and T. Hiyama, Tetrahedron Lett., 1994, 35, 6507; H. Matsuhashi, Y. Hatanaka, M. Kuroboshi and T. Hiyama, Heterocycles, 1996, 42, 375; H. Matsuhashi, S. Asai, K. Hirabayashi, Y. Hatanaka, A. Mori and T. Hiyama, Bull. Chem. Soc. Jpn., 1997, 70, 445; C. Chuit, R. J. P. Corriu, C. Reye and J. C. Young, Chem. Rev., 1993, 93, 1371; K. A. Horn, Chem. Rev., 1995, 95, 1371.
5. T. Hiyama and Y. Hatanaka, Pure Appl. Chem., 1994, 66, 1471; H. Matsuhashi, M. Kuroboshi, Y. Hatanaka and T. Hiyama, Tetrahedron Lett., 1994, 35, 6507; H. Matsuhashi, Y. Hatanaka, M. Kuroboshi and T. Hiyama, Heterocycles, 1996, 42, 375; H. Matsuhashi, S. Asai, K. Hirabayashi, Y. Hatanaka, A. Mori and T. Hiyama, Bull. Chem. Soc. Jpn., 1997, 70, 445; C. Chuit, R. J. P. Corriu, C. Reye and J. C. Young, Chem. Rev., 1993, 93, 1371; K. A. Horn, Chem. Rev., 1995, 95, 1371.
6. T. Hiyama and Y. Hatanaka, Pure Appl. Chem., 1994, 66, 1471; H. Matsuhashi, M. Kuroboshi, Y. Hatanaka and T. Hiyama, Tetrahedron Lett., 1994, 35, 6507; H. Matsuhashi, Y. Hatanaka, M. Kuroboshi and T. Hiyama, Heterocycles, 1996, 42, 375; H. Matsuhashi, S. Asai, K. Hirabayashi, Y. Hatanaka, A. Mori and T. Hiyama, Bull. Chem. Soc. Jpn., 1997, 70, 445; C. Chuit, R. J. P. Corriu, C. Reye and J. C. Young, Chem. Rev., 1993, 93, 1371; K. A. Horn, Chem. Rev., 1995, 95, 1371.
7. H. Matsuhashi, Y. Hatanaka, M. Kuroboshi and T. Hiyama, Tetrahedron Lett., 1995, 36, 1539; E. Hagiwara, K.-i. Gouda, Y. Hatanaka and T. Hiyama, Tetrahedron Lett., 1996, 38, 439.
8. H. Matsuhashi, Y. Hatanaka, M. Kuroboshi and T. Hiyama, Tetrahedron Lett., 1995, 36, 1539; E. Hagiwara, K.-i. Gouda, Y. Hatanaka and T. Hiyama, Tetrahedron Lett., 1996, 38, 439.
9. J.-i. Yoshida, K. Tamao, T. Kakui and M. Kumada, Tetrahedron Lett., 1979, 13, 1141.
10. For reviews on transmetalation in organocopper chemistry, see P. Wipf, Synthesis, 1993, 537 and references cited therein.
11. It has been reported that the allylation of aldehydes with allyltrichlorosilanes could be promoted by DMF or HMPA: S. Kobayashi and K. Nishio, Tetrahedron Lett., 1993, 34, 3453; J. Org. Chem., 1994, 59, 6620; S. E. Denmark, D. M. Coe, N. E., Pratt and B. D. Griedel, J. Org. Chem., 1994, 59, 6161.
12. It has been reported that the allylation of aldehydes with allyltrichlorosilanes could be promoted by DMF or HMPA: S. Kobayashi and K. Nishio, Tetrahedron Lett., 1993, 34, 3453; J. Org. Chem., 1994, 59, 6620; S. E. Denmark, D. M. Coe, N. E., Pratt and B. D. Griedel, J. Org. Chem., 1994, 59, 6161.
13. It has been reported that the allylation of aldehydes with allyltrichlorosilanes could be promoted by DMF or HMPA: S. Kobayashi and K. Nishio, Tetrahedron Lett., 1993, 34, 3453; J. Org. Chem., 1994, 59, 6620; S. E. Denmark, D. M. Coe, N. E., Pratt and B. D. Griedel, J. Org. Chem., 1994, 59, 6161.
14. J. R. Falck, R. K. Bhatt and J. Ye, J. Am. Chem. Soc., 1995, 117, 5973.
15. T. Takeda, K.-i. Matsunaga, Y. Kabasawa and T. Fujiwara, Chem. Lett., 1995, 771; S.-K. Kang, T. Yamaguchi, T.-H. Kim and P.- S. Ho, J. Org. Chem., 1996, 61, 9082.
16. T. Takeda, K.-i. Matsunaga, Y. Kabasawa and T. Fujiwara, Chem. Lett., 1995, 771; S.-K. Kang, T. Yamaguchi, T.-H. Kim and P.- S. Ho, J. Org. Chem., 1996, 61, 9082.
17. J.-i. Yoshida, K. Tamao, A. Kurita and M. Kumada, Tetrahedron Lett., 1978, 1809.
18. J. F. Normant, Synthesis, 1972, 63.
19. For the preparation of 1,3-conjugated diynes, see A. S. Hay, J. Org. Chem., 1962, 27, 3320; G. E. Jones, D. A. Kendrick and A. B. Holmes, Org. Synth., 1987, 65, 52.
20. For the preparation of 1,3-conjugated diynes, see A. S. Hay, J. Org. Chem., 1962, 27, 3320; G. E. Jones, D. A. Kendrick and A. B. Holmes, Org. Synth., 1987, 65, 52.
21. Y. Hatanaka, K. Matsui and T. Hiyama, Tetrahedron Lett., 1989, 30, 2403.