Cross-metathesis of vinylsilanes carrying electron-withdrawing substituents with olefins in the presence of the second-generation Grubbs catalyst

Tetrahedron Letters

Volumn 44, Issue 38, 2003, Pages 7121-7124

  Pietraszuk, Cezary ^a,b   Marciniec, Bogdan ^a   Fischer, Helmut ^b  

^a ADAM MICKIEWICZ UNIVERSITY   (Poland)

^b UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

Cross metathesis; Olefins; Ruthenium; Vinylsilanes

Indexed keywords

1 HEXENE; ALKENE DERIVATIVE; ALLYL COMPOUND; SILANE DERIVATIVE; STYRENE;

ARTICLE; CATALYST; ELECTRON; RING CLOSING METATHESIS; STEREOCHEMISTRY;

EID: 0041508523     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01831-8     Document Type: Article

References (27)

1. For recent reviews, see: (a) Ivin, K. J.; Mol, J. C. Olefin Metathesis and Metathesis Polymerization; Academic Press: San Diego, 1997; (b) Alkene Metathesis in Organic Synthesis; Fürstner, A., Ed.; Springer: Berlin, 1998; (c) Fürstner, A. Angew. Chem. 2000, 112, 3140-3172; Angew. Chem., Int. Ed. 2000, 39, 3012-3043; (d) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565-1604; (e) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
2. For recent reviews, see: (a) Ivin, K. J.; Mol, J. C. Olefin Metathesis and Metathesis Polymerization; Academic Press: San Diego, 1997; (b) Alkene Metathesis in Organic Synthesis; Fürstner, A., Ed.; Springer: Berlin, 1998; (c) Fürstner, A. Angew. Chem. 2000, 112, 3140-3172; Angew. Chem., Int. Ed. 2000, 39, 3012-3043; (d) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565-1604; (e) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
3. For recent reviews, see: (a) Ivin, K. J.; Mol, J. C. Olefin Metathesis and Metathesis Polymerization; Academic Press: San Diego, 1997; (b) Alkene Metathesis in Organic Synthesis; Fürstner, A., Ed.; Springer: Berlin, 1998; (c) Fürstner, A. Angew. Chem. 2000, 112, 3140-3172; Angew. Chem., Int. Ed. 2000, 39, 3012-3043; (d) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565-1604; (e) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
4. For recent reviews, see: (a) Ivin, K. J.; Mol, J. C. Olefin Metathesis and Metathesis Polymerization; Academic Press: San Diego, 1997; (b) Alkene Metathesis in Organic Synthesis; Fürstner, A., Ed.; Springer: Berlin, 1998; (c) Fürstner, A. Angew. Chem. 2000, 112, 3140-3172; Angew. Chem., Int. Ed. 2000, 39, 3012-3043; (d) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565-1604; (e) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
5. For recent reviews, see: (a) Ivin, K. J.; Mol, J. C. Olefin Metathesis and Metathesis Polymerization; Academic Press: San Diego, 1997; (b) Alkene Metathesis in Organic Synthesis; Fürstner, A., Ed.; Springer: Berlin, 1998; (c) Fürstner, A. Angew. Chem. 2000, 112, 3140-3172; Angew. Chem., Int. Ed. 2000, 39, 3012-3043; (d) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565-1604; (e) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
6. For recent reviews, see: (a) Ivin, K. J.; Mol, J. C. Olefin Metathesis and Metathesis Polymerization; Academic Press: San Diego, 1997; (b) Alkene Metathesis in Organic Synthesis; Fürstner, A., Ed.; Springer: Berlin, 1998; (c) Fürstner, A. Angew. Chem. 2000, 112, 3140-3172; Angew. Chem., Int. Ed. 2000, 39, 3012-3043; (d) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565-1604; (e) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
7. For a review, see: Trnka T.M., Grubbs R.H. Acc. Chem. Res. 34:2001;18-29.
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13. For recent reviews on the use of silyl olefins in cross-coupling reactions, see: (a) Hiyama, T. In Metal-Catalysed Cross-Coupling Reactions; Diederich, F.; Stang, P., Eds.; Wiley-VCH: Weinheim, 1998; Chapter 10; (b) Denmark, S. E.; Sweis, R. F. Acc. Chem. Res. 2002, 35, 835-846; (c) Hiyama, T. J. Organomet. Chem. 2002, 653, 58-61.
14. For recent reviews on the use of silyl olefins in cross-coupling reactions, see: (a) Hiyama, T. In Metal-Catalysed Cross-Coupling Reactions; Diederich, F.; Stang, P., Eds.; Wiley-VCH: Weinheim, 1998; Chapter 10; (b) Denmark, S. E.; Sweis, R. F. Acc. Chem. Res. 2002, 35, 835-846; (c) Hiyama, T. J. Organomet. Chem. 2002, 653, 58-61.
15. For recent reviews on the use of silyl olefins in cross-coupling reactions, see: (a) Hiyama, T. In Metal-Catalysed Cross-Coupling Reactions; Diederich, F.; Stang, P., Eds.; Wiley-VCH: Weinheim, 1998; Chapter 10; (b) Denmark, S. E.; Sweis, R. F. Acc. Chem. Res. 2002, 35, 835-846; (c) Hiyama, T. J. Organomet. Chem. 2002, 653, 58-61.
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22. Dialkenylchloromethylsilane and dialkenyldichlorosilane (with silyl group not affecting the double bond) were used in ADMET in the presence of molybdenum carbene complex. See: (a) Cummings, S. K.; Smith, D. W.; Wagener, K. B. Macromol. Rapid. Commun. 1995, 16, 347-355; (b) Anderson, J. D.; Cummings, S.; Portmess, J. D.; Wagener, K. B. Polymer Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1995, 36, 162; (c) Cummings, S.; Anderson, J. D.; Wagener, K. B. Polymer Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1996, 37, 192.
23. Dialkenylchloromethylsilane and dialkenyldichlorosilane (with silyl group not affecting the double bond) were used in ADMET in the presence of molybdenum carbene complex. See: (a) Cummings, S. K.; Smith, D. W.; Wagener, K. B. Macromol. Rapid. Commun. 1995, 16, 347-355; (b) Anderson, J. D.; Cummings, S.; Portmess, J. D.; Wagener, K. B. Polymer Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1995, 36, 162; (c) Cummings, S.; Anderson, J. D.; Wagener, K. B. Polymer Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1996, 37, 192.
24. Dialkenylchloromethylsilane and dialkenyldichlorosilane (with silyl group not affecting the double bond) were used in ADMET in the presence of molybdenum carbene complex. See: (a) Cummings, S. K.; Smith, D. W.; Wagener, K. B. Macromol. Rapid. Commun. 1995, 16, 347-355; (b) Anderson, J. D.; Cummings, S.; Portmess, J. D.; Wagener, K. B. Polymer Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1995, 36, 162; (c) Cummings, S.; Anderson, J. D.; Wagener, K. B. Polymer Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1996, 37, 192.
25. Pawlenko S. Organosilicon Chemistry. 1986;Walter de Gruyter, Berlin.
26. 2), 113.9 (=CHSi), 156.0 (=CH), 168.9 (Ac).
27. For the mechanism of the decomposition of I in the presence of vinyltrimethylsilane, see: Pietraszuk C., Fischer H. Chem. Commun. 2000;2463-2464.