Cu(I)/Pd(0)-catalyzed cross-coupling reaction of alkynylsilanes with aryl or alkenyl triflates: "Sila"-Sonogashira-Hagihara coupling

Chemistry Letters

Volumn , Issue 12, 1997, Pages 1233-1234

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

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000008560     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.1233     Document Type: Article

References (17)

1. For general reviews on palladium-catalyzed coupling reactions, see: K. Tamao, "Comprehensive Organic Synthesis", ed by B. M. Trost, Pergamon Press, Inc., New York, Vol. 3, p 435 (1991); J. Tsuji, "Palladium Reagents and Catalysts. Innovation in Organic Synthesis", John Wiley and Sons: Chichester, pp 19-124 (1995).
2. For general reviews on palladium-catalyzed coupling reactions, see: K. Tamao, "Comprehensive Organic Synthesis", ed by B. M. Trost, Pergamon Press, Inc., New York, Vol. 3, p 435 (1991); J. Tsuji, "Palladium Reagents and Catalysts. Innovation in Organic Synthesis", John Wiley and Sons: Chichester, pp 19-124 (1995).
3. R. D. Stephens and C. E. Castro, J. Org. Chem., 28, 3313 (1963).
4. E.-i. Negishi, Acc. Chem. Res., 15, 340 (1982).
5. J. K. Stille, Angew. Chem. Int. Ed. Engl., 25, 508 (1986).
6. K. Sonogashira, Y. Tohda, and N. Hagihara, Tetrahedron Lett. 1975, 4467; S. Takahashi, Y. Kuroyama, K. Sonogashira, and N. Hagihara, Synthesis 1980, 627; I. B. Campbell, The Sonogashira Cu-Pd-catalyzed alkyne coupling reaction in "Organocopper Reagents A Practical Approach"; ed by R. J. K. Taylor, Oxford University Press, Oxford, pp 217-235 (1994).
7. K. Sonogashira, Y. Tohda, and N. Hagihara, Tetrahedron Lett. 1975, 4467; S. Takahashi, Y. Kuroyama, K. Sonogashira, and N. Hagihara, Synthesis 1980, 627; I. B. Campbell, The Sonogashira Cu-Pd-catalyzed alkyne coupling reaction in "Organocopper Reagents A Practical Approach"; ed by R. J. K. Taylor, Oxford University Press, Oxford, pp 217-235 (1994).
8. K. Sonogashira, Y. Tohda, and N. Hagihara, Tetrahedron Lett. 1975, 4467; S. Takahashi, Y. Kuroyama, K. Sonogashira, and N. Hagihara, Synthesis 1980, 627; I. B. Campbell, The Sonogashira Cu-Pd-catalyzed alkyne coupling reaction in "Organocopper Reagents A Practical Approach"; ed by R. J. K. Taylor, Oxford University Press, Oxford, pp 217-235 (1994).
9. K. Ikegashira, Y. Nishihara, K. Hirabayashi, A. Mori, and T. Hiyama, Chem. Commun., 1997, 1039.
10. Several papers on the observation of transmetalation from silicon to copper have appeared recently, F. Babudri, A. R. Cicciomessere, G. M. Farinola, V. Fiandanese, G. Marchese, R. Musio, F. Naso, and O. Sciacovelli, J. Org. Chem., 62, 3291 (1997); See also: H. Ito, K. Arimoto, H.-o. Sensui, and A. Hosomi, Tetrahedron Lett., 38, 3977 (1997); S.-K. Kang, T.-H. Kim, and S.-J. Pyun, J. Chem. Soc., Perkin Trans., 1, 1997, 797.
11. Several papers on the observation of transmetalation from silicon to copper have appeared recently, F. Babudri, A. R. Cicciomessere, G. M. Farinola, V. Fiandanese, G. Marchese, R. Musio, F. Naso, and O. Sciacovelli, J. Org. Chem., 62, 3291 (1997); See also: H. Ito, K. Arimoto, H.-o. Sensui, and A. Hosomi, Tetrahedron Lett., 38, 3977 (1997); S.-K. Kang, T.-H. Kim, and S.-J. Pyun, J. Chem. Soc., Perkin Trans., 1, 1997, 797.
12. Several papers on the observation of transmetalation from silicon to copper have appeared recently, F. Babudri, A. R. Cicciomessere, G. M. Farinola, V. Fiandanese, G. Marchese, R. Musio, F. Naso, and O. Sciacovelli, J. Org. Chem., 62, 3291 (1997); See also: H. Ito, K. Arimoto, H.-o. Sensui, and A. Hosomi, Tetrahedron Lett., 38, 3977 (1997); S.-K. Kang, T.-H. Kim, and S.-J. Pyun, J. Chem. Soc., Perkin Trans., I, 1997, 797.
13. As we reported in the homo-coupling of organosilanes (ref 5), CuCl or Cu(OTf) were found to be a favorable Cu(I) salt to effect the transmetalation from silicon to copper. Subsequently, the use of triflate as a leaving group was necessary to generate Cu(OTf) in the catalytic system.
14. 2 10 The reaction of 1b with 2d gave 5d in 27% yield.
15. Y. Hatanaka and T. Hiyama, J. Org. Chem., 53, 918 (1988); Y. Hatanaka, K. Matsui, and T. Hiyama, Tetrahedron Lett., 30, 2403 (1989).
16. Y. Hatanaka and T. Hiyama, J. Org. Chem., 53, 918 (1988); Y. Hatanaka, K. Matsui, and T. Hiyama, Tetrahedron Lett., 30, 2403 (1989).
17. The cross-coupling reaction of aryl triflates with terminal acetylenes in the absence of CuI is reported by Q.-Y Chen and Z.-Y. Yang, Tetrahedron Lett., 27, 1171 (1986).