Issue 6, 2014

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
25 Apr 2014
Accepted
20 May 2014
First published
28 May 2014
This article is Open Access
Creative Commons BY license

Org. Chem. Front., 2014,1, 661-673

Author version available

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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