PDF icon Download PDF
Synthesis 2012(4): 575-578  
DOI: 10.1055/s-0031-1289669
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Specific Polar Solvents as Organocatalysts for the Hydrosilylation of Isoprene

Arno Behr*, Sebastian Reyer, Yvonne Brunsch, Vanessa Manz
Department of Biochemical and Chemical Engineering, Technische Universität Dortmund, Emil-Figge Str. 66, 44227 Dortmund, Germany
Fax: +49(231)7552311; e-Mail: behr@bci.tu-dortmund.de.;
Further Information

Publication History

Received 9 September 2011
Publication Date:
16 January 2012 (online)

   Permissions and Reprints All articles of this category
Preview

Abstract

Isoprene was hydrosilylated in the absence of transition metals by using specific organic solvents as both reaction media and organocatalysts. A highly selective reaction with successful catalyst recycling could be performed by using propylene carbonate as the reaction medium.

Key words

hydrosilylations - homogeneous catalysis - solvent effects - dienes - silanes

    References

  • 1 Marciniec B. Guliński G. J. Organomet. Chem.  1993,  446:  15 
    Search in Google Scholar
  • 2 Brockmann M. Dieck HT. Kleinwächter I.
    J. Organomet. Chem.  1986,  309:  345 
    Search in Google Scholar
  • 3 Gustafsson M. Frejd T. J. Chem. Soc., Perkin Trans. 1  2002,  102 
  • 4 Gustafsson M. Frejd T. J. Organomet. Chem.  2004,  689:  438 
    Search in Google Scholar
  • 5 Michalska ZM. Ostaszewski B. Strzelec K.
    J. Organomet. Chem.  1995,  496:  19 
    Search in Google Scholar
  • 6 Ojima I. Donovan RJ. Clos N. Organometallics  1991,  10:  2606 
    Search in Google Scholar
  • 7 Benkeser RA. Merritt FM. Roche RT. J. Organomet. Chem.  1978,  156:  235 
    Search in Google Scholar
  • 8 Hilt G. Lüers S. Schmidt F. Synthesis  2003,  634 
  • 9 Abdelqader W. Chmielewski D. Grevels F.-W. Özkar S. Peynircioglu NB. Organometallics  1996,  15:  604 
    Search in Google Scholar
  • 10 Kayran C. Rouzi P. Z. Naturforsch., B  2001,  56:  1138 
    Search in Google Scholar
  • 11 Kayran C. Özkar S. Akhmedov VM. Z. Naturforsch., B  2003,  58:  644 
    Search in Google Scholar
  • 12 Takaki K. Sonoda K. Kousaka T. Koshoji G. Shishido T. Takehira K. Tetrahedron Lett.  2001,  42:  9211 
    Search in Google Scholar
  • 13 Tamao K. Miyake N. Kiso Y. Kumada M. J. Am. Chem. Soc.  1975,  97:  5603 
    Search in Google Scholar
  • 14 Tanaka M. Uchimaru Y. Lautenschlager HJ. Organometallics  1991,  10:  16 
    Search in Google Scholar
  • 15 Tanaka M. Uchimaru Y. Lautenschlager HJ.
    J. Organomet. Chem.  1992,  428:  1 
    Search in Google Scholar
  • 16 Terao J. Kambe N. Sonoda N. Tetrahedron Lett.  1998,  39:  9697 
    Search in Google Scholar
  • 17 Stammer A, and Wolf FTA. inventors; WO  2008125561. 
  • 18 Maegawa Y. Mizoshita N. Tani T. Shimada T. Inagaki S. J. Mater. Chem.  2011,  21:  14020 
    Search in Google Scholar
  • 19 Han J.-W. Hayashi T. Tetrahedron: Asymmetry  2010,  21:  2193 
    Search in Google Scholar
  • 20 Fleming I. Barbero A. Walter D. Chem. Rev.  1997,  97:  2063 
    Search in Google Scholar
  • 21 Riant O. In Modern Reduction Methods   Andersson PG. Munslow IJ. Wiley-VCH; Weinheim: 2008.  Chap. 13. p.321 
  • 22 Rendler S. Oestreich M. In Modern Reduction Methods   Andersson PG. Munslow IJ. Wiley-VCH; Weinheim: 2008.  Chap. 8. p.183 
  • 23 Roy AK. Adv. Organomet. Chem.  2008,  55:  1 
    Search in Google Scholar
  • 24 Fonseca MH. List B. Curr. Opin. Chem. Biol.  2004,  8:  319 
    Search in Google Scholar