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. 2013 Sep 11;135(36):13330-3.
doi: 10.1021/ja407748z. Epub 2013 Aug 28.

Preparation of vinyl silyl ethers and disiloxanes via the silyl-Heck reaction of silyl ditriflates

Sara E S Martin  1 , Donald A Watson
Affiliations

Preparation of vinyl silyl ethers and disiloxanes via the silyl-Heck reaction of silyl ditriflates

Sara E S Martin et al. J Am Chem Soc. .

Abstract

Vinyl silyl ethers and disiloxanes can now be prepared from aryl-substituted alkenes and related substrates using a silyl-Heck reaction. The reaction employs a commercially available catalyst system and mild conditions. This work represents a highly practical means of accessing diverse classes of vinyl silyl ether substrates in an efficient and direct manner with complete regiomeric and geometric selectivity.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Preparation of Vinyl Silyl Ethers From Alkenes
Scheme 1
Scheme 1
Silyl-Heck/Hiyama-Denmark vs. Direct Heck
Scheme 2
Scheme 2. Preparation of Diverse Vinyl Silanes
a1.25 mol % Pd2(dba)3, 5.5 mol % tBuPPh2, 1.1 equiv Me2Si(OTf)2 5 mol % NaI, Et3N, PhMe, 35 °C
See this image and copyright information in PMC

References

    1. Fleming I, Barbero A, Walter D. Chem Rev. 1997;97:2063–2192. - PubMed
    2. Brook MA. Silicon in Organic, Organometallic, and Polymer Chemistry. Wiley; Chichester: 2000.
    3. Fleming I, Dunoguès J, Smithers R. Organic Reactions. John Wiley & Sons, Inc; 2004. The Electrophilic Substitution of Allylsilanes and Vinylsilanes; pp. 57–575.
    1. Nakao Y, Hiyama T. Chem Soc Rev. 2011;40:4893–4901. - PubMed
    1. Denmark SE, Regens CS. Acc Chem Res. 2008;41:1486–1499. - PMC - PubMed
    2. Denmark SE, Liu JHC. Angew Chem Int Ed. 2010;49:2978–2986. - PMC - PubMed
    3. Sore HF, Galloway WRJD, Spring DR. Chem Soc Rev. 2012;41:1845–1866. - PubMed
    1. Jones GR, Landais Y. Tetrahedron. 1996;52:7599–7662.
    1. Oshima K. Vinylsilanes. In: Fleming I, editor. Science of Synthesis. Vol. 4. Thieme; Stuttgart: 2001. pp. 713–754.
    2. Denmark SE, Neuville L, Christy MEL, Tymonko SA. J Org Chem. 2006;71:8500–8509. - PubMed

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