Synlett 2013; 24(17): 2177-2182
DOI: 10.1055/s-0033-1339795
synpacts
© Georg Thieme Verlag Stuttgart · New York

Silyl-Heck Reactions for the Preparation of Unsaturated Organosilanes

Sara E. S. Martin
Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA   Fax: +1(302)8316335   Email: dawatson@udel.edu
,
Donald A. Watson*
Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA   Fax: +1(302)8316335   Email: dawatson@udel.edu
› Author Affiliations
Further Information

Publication History

Received: 22 July 2013

Accepted after revision: 16 August 2013

Publication Date:
30 September 2013 (online)

Abstract

Few methods exist to directly install silyl functionality onto olefins. This Synpacts article highlights the state of the art of the silyl-Heck reaction and our recently developed conditions for preparing allyl and vinyl silanes from terminal alkenes using this method.

 
  • References

    • 2a Nakao Y, Hiyama T. Chem. Soc. Rev. 2011; 40: 4893
    • 2b Denmark SE, Liu JH.-C. Angew. Chem. Int. Ed. 2010; 49: 2978
    • 3a Hosomi A, Endo M, Sakurai H. Chem. Lett. 1976; 5: 941
    • 3b Masse CE, Panek JS. Chem. Rev. 1995; 95: 1293
    • 3c Denmark SE, Fu J. Chem. Rev. 2003; 103: 2763
    • 5a Bourque L, Cleary P, Woerpel KA. J. Am. Chem. Soc. 2007; 129: 12602
    • 5b Moser R, Nishikata T, Lipshutz BH. Org. Lett. 2010; 12: 28
    • 5c Selander N, Paasch JR, Szabó KJ. J. Am. Chem. Soc. 2011; 133: 409
  • 6 Murakami K, Yorimitsu H, Oshima K. J. Org. Chem. 2009; 74: 1415
    • 7a Trost BM, Ball ZT. J. Am. Chem. Soc. 2005; 127: 17644
    • 7b Berthon-Gelloz G, Schumers J.-M, De Bo G, Markó IE. J. Org. Chem. 2008; 73: 4190
    • 8a Marciniec B, Pietraszuk C. Top. Organomet. Chem. 2004; 11: 197
    • 8b Ohmiya H, Yorimitsu H, Oshima K. Org. Lett. 2006; 8: 3093
    • 9a Marciniec B. Coord. Chem. Rev. 2005; 249: 2374
    • 9b Terao J, Torii K, Saito K, Kambe N, Baba A, Sonoda N. Angew. Chem. Int. Ed. 1998; 37: 2653
    • 9c Jiang Y, Blacque O, Fox T, Frech CM, Berke H. Chem. Eur. J. 2009; 15: 2121
    • 9d Lu B, Falck J. J. Org. Chem. 2010; 75: 1701
    • 9e Cheng C, Simmons EM, Hartwig JF. Angew. Chem. Int. Ed. 2013; 52: 8984
  • 10 Oestreich M. The Mizoroki–Heck Reaction . John Wiley and Sons; Chichester: 2008: 568
  • 11 McAtee JR, Martin SE. S, Ahneman DT, Johnson KA, Watson DA. Angew. Chem. Int. Ed. 2012; 51: 3663
  • 12 Yamashita H, Hayashi T, Kobayashi T, Tanaka M, Goto M. J. Am. Chem. Soc. 1988; 110: 4417
  • 13 Armitage DA In Comprehensive Organometallic Synthesis . Vol. 2. Wilkinson G, Stone FG. A, Abel EW. Pergamon; Oxford: 1982: 6
  • 14 Yamashita H, Tanaka M, Goto M. Organometallics 1997; 16: 4696
  • 15 Yamashita H, Kobayashi T, Hayashi T, Tanaka M. Chem. Lett. 1991; 20: 761
  • 16 Drahl C. Chem. Eng. News 2012; 90 (14): 9
  • 17 Hiyama T, Shirakawa E. Organosilicon Compounds . In Cross-Coupling Reactions . Vol. 219. Miyaura N. Springer; Berlin/Heidelberg: 2002: 61-85
  • 18 Pawluć P, Szudkowska J, Hreczycho G, Marciniec B. J. Org. Chem. 2011; 76: 6438
    • 19a Greedy B, Gouverneur V. Chem. Commun. 2001; 233
    • 19b Ranjbar-Karimi R. Ultrason. Sonochem. 2010; 17: 768
  • 20 Hayashi T, Kabeta K, Hamachi I, Kumada M. Tetrahedron Lett. 1983; 24: 2865
  • 21 Fleming I, Lewis JJ. J. Chem. Soc., Perkin Trans. 1 1992; 3267
  • 22 Terao J, Jin Y, Torii K, Kambe N. Tetrahedron 2004; 60: 1301