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Issue 6, 2014
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Carbopalladation of bromoene-alkynylsilanes: mechanistic insights and synthesis of fused-ring bicyclic silanes and phenols

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Abstract

The palladium-catalyzed cascade cyclization of silylated bromoenynes and alkenylstannanes provides a straightforward route to a range of bicyclic silylated cyclohexadienes. Mechanistic insights into aspects of carbopalladation and unusual palladium-mediated isomerizations have been obtained through the detection of reaction intermediates, the isolation of byproducts, and reaction monitoring by VT NMR spectroscopy. The utility of the bicyclic products is illustrated through oxidation to bicyclic enones and phenols.

Graphical abstract: Carbopalladation of bromoene-alkynylsilanes: mechanistic insights and synthesis of fused-ring bicyclic silanes and phenols

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Publication details

The article was received on 25 Apr 2014, accepted on 20 May 2014 and first published on 28 May 2014


Article type: Research Article
DOI: 10.1039/C4QO00123K
Citation: Org. Chem. Front., 2014,1, 661-673
  • Open access: Creative Commons BY license
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    Carbopalladation of bromoene-alkynylsilanes: mechanistic insights and synthesis of fused-ring bicyclic silanes and phenols

    M. A. Cordonnier, S. B. J. Kan, B. Gockel, S. S. Goh and E. A. Anderson, Org. Chem. Front., 2014, 1, 661
    DOI: 10.1039/C4QO00123K

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