Stereoselective synthesis of (Z)-1-Silyl-2-stannylethene by palladium-catalyzed silastannation of ethyne and its synthetic transformations

Synthesis

Volumn , Issue 9, 2004, Pages 1522-1526

  Murakami, Masahiro ^a   Matsuda, Takanori ^a   Itami, Kenichiro ^a   Ashida, Shinji ^a   Terayama, Miki ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Alkyne; cis addition; Cross coupling; Palladium; Silylstannane

Indexed keywords

CATALYSIS; CATALYSTS; HYDROCARBONS; SYNTHESIS (CHEMICAL);

ETHYNE; SYNTHETIC UTILITIES;

PALLADIUM COMPOUNDS;

ACETYLENE; CYANIDE; ETHYLENE; PALLADIUM;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 3042793632     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-822405     Document Type: Article

References (35)

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14. For palladium-catalyzed silastannation of alkynes see: (a) Mitchell, T. N.; Killing, H.; Dicke, R.; Wickenkamp, R. J. Chem. Soc., Chem. Commun. 1985, 354. (b) Chenard, B. L.; Laganis, E. D.; Davidson, F.; RajanBabu, T. V. J. Org. Chem. 1985, 50, 3666. (c) Chenard, B. L.; Van Zyl, C. M. J. Org. Chem. 1986, 51, 3561. (d) Mitchell, T. N.; Wickenkamp, R.; Amamria, A.; Dicke, R.; Schneider, U. J. Org. Chem. 1987, 52, 4868. (e) Ritter, K. Synthesis 1989, 218. (f) Casson, S.; Kocienski, P. J.; Reid, G.; Smith, N.; Street, J. M.; Webster, M. Synthesis 1994, 1301. (g) Lunot, S.; Thibonnet, J.; Duchêne, A.; Parrain, J.-L.; Abarbri, M. Tetrahedron Lett. 2000, 41, 8893. (h) Minière, S.; Cintrat, J.-C. Synthesis 2001, 705. (i) Hemeon, I.; Singer, R. D. Chem. Commun. 2002, 1884. (j) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391.
15. For palladium-catalyzed silastannation of alkynes see: (a) Mitchell, T. N.; Killing, H.; Dicke, R.; Wickenkamp, R. J. Chem. Soc., Chem. Commun. 1985, 354. (b) Chenard, B. L.; Laganis, E. D.; Davidson, F.; RajanBabu, T. V. J. Org. Chem. 1985, 50, 3666. (c) Chenard, B. L.; Van Zyl, C. M. J. Org. Chem. 1986, 51, 3561. (d) Mitchell, T. N.; Wickenkamp, R.; Amamria, A.; Dicke, R.; Schneider, U. J. Org. Chem. 1987, 52, 4868. (e) Ritter, K. Synthesis 1989, 218. (f) Casson, S.; Kocienski, P. J.; Reid, G.; Smith, N.; Street, J. M.; Webster, M. Synthesis 1994, 1301. (g) Lunot, S.; Thibonnet, J.; Duchêne, A.; Parrain, J.-L.; Abarbri, M. Tetrahedron Lett. 2000, 41, 8893. (h) Minière, S.; Cintrat, J.-C. Synthesis 2001, 705. (i) Hemeon, I.; Singer, R. D. Chem. Commun. 2002, 1884. (j) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391.
16. For palladium-catalyzed silastannation of alkynes see: (a) Mitchell, T. N.; Killing, H.; Dicke, R.; Wickenkamp, R. J. Chem. Soc., Chem. Commun. 1985, 354. (b) Chenard, B. L.; Laganis, E. D.; Davidson, F.; RajanBabu, T. V. J. Org. Chem. 1985, 50, 3666. (c) Chenard, B. L.; Van Zyl, C. M. J. Org. Chem. 1986, 51, 3561. (d) Mitchell, T. N.; Wickenkamp, R.; Amamria, A.; Dicke, R.; Schneider, U. J. Org. Chem. 1987, 52, 4868. (e) Ritter, K. Synthesis 1989, 218. (f) Casson, S.; Kocienski, P. J.; Reid, G.; Smith, N.; Street, J. M.; Webster, M. Synthesis 1994, 1301. (g) Lunot, S.; Thibonnet, J.; Duchêne, A.; Parrain, J.-L.; Abarbri, M. Tetrahedron Lett. 2000, 41, 8893. (h) Minière, S.; Cintrat, J.-C. Synthesis 2001, 705. (i) Hemeon, I.; Singer, R. D. Chem. Commun. 2002, 1884. (j) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391.
17. For palladium-catalyzed silastannation of alkynes see: (a) Mitchell, T. N.; Killing, H.; Dicke, R.; Wickenkamp, R. J. Chem. Soc., Chem. Commun. 1985, 354. (b) Chenard, B. L.; Laganis, E. D.; Davidson, F.; RajanBabu, T. V. J. Org. Chem. 1985, 50, 3666. (c) Chenard, B. L.; Van Zyl, C. M. J. Org. Chem. 1986, 51, 3561. (d) Mitchell, T. N.; Wickenkamp, R.; Amamria, A.; Dicke, R.; Schneider, U. J. Org. Chem. 1987, 52, 4868. (e) Ritter, K. Synthesis 1989, 218. (f) Casson, S.; Kocienski, P. J.; Reid, G.; Smith, N.; Street, J. M.; Webster, M. Synthesis 1994, 1301. (g) Lunot, S.; Thibonnet, J.; Duchêne, A.; Parrain, J.-L.; Abarbri, M. Tetrahedron Lett. 2000, 41, 8893. (h) Minière, S.; Cintrat, J.-C. Synthesis 2001, 705. (i) Hemeon, I.; Singer, R. D. Chem. Commun. 2002, 1884. (j) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391.
18. For palladium-catalyzed silastannation of alkynes see: (a) Mitchell, T. N.; Killing, H.; Dicke, R.; Wickenkamp, R. J. Chem. Soc., Chem. Commun. 1985, 354. (b) Chenard, B. L.; Laganis, E. D.; Davidson, F.; RajanBabu, T. V. J. Org. Chem. 1985, 50, 3666. (c) Chenard, B. L.; Van Zyl, C. M. J. Org. Chem. 1986, 51, 3561. (d) Mitchell, T. N.; Wickenkamp, R.; Amamria, A.; Dicke, R.; Schneider, U. J. Org. Chem. 1987, 52, 4868. (e) Ritter, K. Synthesis 1989, 218. (f) Casson, S.; Kocienski, P. J.; Reid, G.; Smith, N.; Street, J. M.; Webster, M. Synthesis 1994, 1301. (g) Lunot, S.; Thibonnet, J.; Duchêne, A.; Parrain, J.-L.; Abarbri, M. Tetrahedron Lett. 2000, 41, 8893. (h) Minière, S.; Cintrat, J.-C. Synthesis 2001, 705. (i) Hemeon, I.; Singer, R. D. Chem. Commun. 2002, 1884. (j) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391.
19. For palladium-catalyzed silastannation of alkynes see: (a) Mitchell, T. N.; Killing, H.; Dicke, R.; Wickenkamp, R. J. Chem. Soc., Chem. Commun. 1985, 354. (b) Chenard, B. L.; Laganis, E. D.; Davidson, F.; RajanBabu, T. V. J. Org. Chem. 1985, 50, 3666. (c) Chenard, B. L.; Van Zyl, C. M. J. Org. Chem. 1986, 51, 3561. (d) Mitchell, T. N.; Wickenkamp, R.; Amamria, A.; Dicke, R.; Schneider, U. J. Org. Chem. 1987, 52, 4868. (e) Ritter, K. Synthesis 1989, 218. (f) Casson, S.; Kocienski, P. J.; Reid, G.; Smith, N.; Street, J. M.; Webster, M. Synthesis 1994, 1301. (g) Lunot, S.; Thibonnet, J.; Duchêne, A.; Parrain, J.-L.; Abarbri, M. Tetrahedron Lett. 2000, 41, 8893. (h) Minière, S.; Cintrat, J.-C. Synthesis 2001, 705. (i) Hemeon, I.; Singer, R. D. Chem. Commun. 2002, 1884. (j) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391.
20. For palladium-catalyzed silastannation of alkynes see: (a) Mitchell, T. N.; Killing, H.; Dicke, R.; Wickenkamp, R. J. Chem. Soc., Chem. Commun. 1985, 354. (b) Chenard, B. L.; Laganis, E. D.; Davidson, F.; RajanBabu, T. V. J. Org. Chem. 1985, 50, 3666. (c) Chenard, B. L.; Van Zyl, C. M. J. Org. Chem. 1986, 51, 3561. (d) Mitchell, T. N.; Wickenkamp, R.; Amamria, A.; Dicke, R.; Schneider, U. J. Org. Chem. 1987, 52, 4868. (e) Ritter, K. Synthesis 1989, 218. (f) Casson, S.; Kocienski, P. J.; Reid, G.; Smith, N.; Street, J. M.; Webster, M. Synthesis 1994, 1301. (g) Lunot, S.; Thibonnet, J.; Duchêne, A.; Parrain, J.-L.; Abarbri, M. Tetrahedron Lett. 2000, 41, 8893. (h) Minière, S.; Cintrat, J.-C. Synthesis 2001, 705. (i) Hemeon, I.; Singer, R. D. Chem. Commun. 2002, 1884. (j) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391.
21. For palladium-catalyzed silastannation of alkynes see: (a) Mitchell, T. N.; Killing, H.; Dicke, R.; Wickenkamp, R. J. Chem. Soc., Chem. Commun. 1985, 354. (b) Chenard, B. L.; Laganis, E. D.; Davidson, F.; RajanBabu, T. V. J. Org. Chem. 1985, 50, 3666. (c) Chenard, B. L.; Van Zyl, C. M. J. Org. Chem. 1986, 51, 3561. (d) Mitchell, T. N.; Wickenkamp, R.; Amamria, A.; Dicke, R.; Schneider, U. J. Org. Chem. 1987, 52, 4868. (e) Ritter, K. Synthesis 1989, 218. (f) Casson, S.; Kocienski, P. J.; Reid, G.; Smith, N.; Street, J. M.; Webster, M. Synthesis 1994, 1301. (g) Lunot, S.; Thibonnet, J.; Duchêne, A.; Parrain, J.-L.; Abarbri, M. Tetrahedron Lett. 2000, 41, 8893. (h) Minière, S.; Cintrat, J.-C. Synthesis 2001, 705. (i) Hemeon, I.; Singer, R. D. Chem. Commun. 2002, 1884. (j) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391.
22. For palladium-catalyzed silastannation of alkynes see: (a) Mitchell, T. N.; Killing, H.; Dicke, R.; Wickenkamp, R. J. Chem. Soc., Chem. Commun. 1985, 354. (b) Chenard, B. L.; Laganis, E. D.; Davidson, F.; RajanBabu, T. V. J. Org. Chem. 1985, 50, 3666. (c) Chenard, B. L.; Van Zyl, C. M. J. Org. Chem. 1986, 51, 3561. (d) Mitchell, T. N.; Wickenkamp, R.; Amamria, A.; Dicke, R.; Schneider, U. J. Org. Chem. 1987, 52, 4868. (e) Ritter, K. Synthesis 1989, 218. (f) Casson, S.; Kocienski, P. J.; Reid, G.; Smith, N.; Street, J. M.; Webster, M. Synthesis 1994, 1301. (g) Lunot, S.; Thibonnet, J.; Duchêne, A.; Parrain, J.-L.; Abarbri, M. Tetrahedron Lett. 2000, 41, 8893. (h) Minière, S.; Cintrat, J.-C. Synthesis 2001, 705. (i) Hemeon, I.; Singer, R. D. Chem. Commun. 2002, 1884. (j) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391.
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26. The reaction failed to proceed effectively at room temperature.
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28. It was formed via disproportionation of silylstannane to distannane followed by bis-stannation of ethyne. For bisstannation of ethyne see: (a) Mitchell, T. N.; Killing, A. A. H.; Rutschow, D. J. Organomet. Chem. 1983, 241, C45. (b) Mitchell, T. N.; Killing, A. A. H.; Rutschow, D. J. Organomet. Chem. 1986, 304, 257.
29. Interestingly, the reaction with trimethyl(dimethylphenylsilyl)stannane in place of 1b gave no silastannation product at all. Instead, 1,2-diphenyltetramethyldisilane was formed by disproportionation.
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