Abstract
Applications of the catalytic transformations of vinyl group at silicon, i.e., cross-metathesis, silylative coupling with olefins and silylative coupling with acetylenes for functionalisation of vinylsubstituted (poly)organosiloxanes were overviewed. Cross-metathesis and silylative coupling of olefins with vinylsilicon compounds catalysed by ruthenium complexes were shown to constitute two valuable, complementary synthetic routes leading to functionalised (poly)siloxanes, cyclosiloxanes, silsesquioxanes and spherosilicates of great practical importance. Moreover, first examples of selective synthesis of variety of siloxanes with acetylene functionality via silylative coupling of acetylenes with vinylsiloxanes were described.
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References
Chan TH, Fleming I (1979) Synthesis 761;
Weber WP (1983) Silicon reagents for organic synthesis, Ch 7. Springer, Berlin;
Colvin EW (1988) Silicon reagents in organic synthesis Ch 3. Academic Press, London;
Luh T-Y, Liu S-T (1998) In: Rappoport Z, Apeloig Y (eds.) The chemistry of organosilicon compounds. Wiley, Chichester
Denmark SE, Sweis RF (2004) Organosilicon compounds in cross-coupling reaction. In: de Meijere A, Diederich F (eds.) Metal-catalysed cross-coupling reactions, Wiley-VCH, Weinheim;
Denmark SE, Ober MH (2003) Aldrichim Acta 36: 75–85
Boutevin F, Guida-Pietrasanta F, Ratsimihety A (2000) Side group modified polysiloxanes. In: Jones RG, Ando W, Chojnowski J (eds.) Silicon containing polymers, Kluwer, Dordrecht
Baney RH, Itoh M, Sakakibara A, Suzuki T (1995) Chem Rev 95: 1409–1430
Marciniec B, Pietraszuk C (2003) Metathesis of silicon-containing olefins. In: Grubbs RH (ed.) Handbook of metathesis, Wiley-VCH, Weinheim;
Marciniec B, Pietraszuk C (2000) Curr Org Chem 7: 691–743;
Marciniec B (2005) Coord Chem Rev 249: 2374–2390
Grubbs RH (ed.) (2003) Handbook of metathesis, Wiley-VCH, Weinheim
Pietraszuk C, Marciniec B, Fischer H (2000) Organometallics 29: 913–917;
Pietraszuk C, Fischer H, Kujawa M, Marciniec B (2001) Tetrahedron Lett 42: 1175–1178;
Pietraszuk C, Marciniec B, Fischer H (2003) Tetrahedron Lett 44: 7121–7124
Pietraszuk C, Fischer H (2000) Chem Commun 2463–2464
Wakatsuki Y, Yamazaki H, Nakano M, Yamamoto Y (1991) J Chem Soc Chem Commun 703–704;
Marciniec B, Pietraszuk C (1995) J Chem Soc Chem Commun 2003–2004;
Marciniec B, Pietraszuk C (1997) Organometallics 16: 4320–4326
Marciniec B, Dudziec B, Kownacki I (2006) Angew Chem Int Ed 45: 8180–8184;
Pol. Pat. Appl. 380422;
WO 2008020774;
Marciniec B (2007) Acc Chem Res 40: 943–952
Zak P, Pietraszuk C, Marciniec B (2008) J Mol Catal A: Chem 285: 101–108
Marciniec B, Pietraszuk C, Kujawa M (1998) J Mol Catal A: Chem. 133: 41–49
Zak P, Skrobanska M, Pietraszuk C, Marciniec B (2008) Organometallics (submitted)
Pat PL 195453
Pietraszuk C, Rogalski S, Majchrzak M, Marciniec B (2006) J Organomet Chem 691: 5476–5481
Marciniec B, Walczuk-Gusciora E, Pietraszuk C (2001) Organometallics 20: 3423–3428
Prukala W, Marciniec B, Majchrzak M, Kubicki M (2007) Tetrahedron 63: 1107–1115
Marciniec B, Kujawa M, Pietraszuk C (2000) Organometallics 19: 1677–1681
Itami Y, Marciniec B, Kubicki M (2003) Organometallics 22: 3717–3722
Marciniec B, Waehner J, Pawluc P, Kubicki M (2007) J Mol Catal A: Chem 265: 25–31
Dudziec B, Marciniec B (2008) Organometallics 27: 5598–5604
Feher FJ, Soulivong D, Eklund AG, Wydham KD (1997) Chem Commun 1185–1186
Itami Y, Marciniec B, Kubicki M (2004) Chem Eur J 10: 1239–1248
Waehner J, Marciniec B, Pawluc P (2007) Eur J Inorg Chem 2975–2980
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Marciniec, B., Pietraszuk, C. (2010). Functionalisation of Vinylsubstituted (Poly)Siloxanes and Silsesquioxanes via Cross-Metathesis and Silylative Coupling Transformations. In: Dragutan, V., Demonceau, A., Dragutan, I., Finkelshtein, E.S. (eds) Green Metathesis Chemistry. NATO Science for Peace and Security Series A: Chemistry and Biology. Springer, Dordrecht. https://doi.org/10.1007/978-90-481-3433-5_12
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DOI: https://doi.org/10.1007/978-90-481-3433-5_12
Publisher Name: Springer, Dordrecht
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