Synfacts 2007(4): 0421-0421  
DOI: 10.1055/s-2007-968323
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Silylmetallation of Functionalized Terminal Alkenes

Contributor(s): Paul Knochel, Tobias Thaler
S. Nakamura*, M. Uchiyama*
The University of Tokyo and Institute of Physical and Chemical Research, Saitama, Japan
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Publikationsverlauf

Publikationsdatum:
23. März 2007 (online)

Significance

The chemo- and regioselective silyl­metallation of terminal alkenes which is mediated by a system consisting of SiBNOL-Zn-ate and catalytic CuCN is an extremely valuable development. The reaction is applicable to a broad range of functionalized terminal alkenes. The silyl­ation occurs regioselectively with monosubstituted alkenes at the terminal carbon atom. If two C-C double bonds are present in a molecule, silyl­metallation takes place at the double bond with the smallest number of substituents. The alkylmetal intermediates can be trapped with a number of electrophiles, leading to a variety of functionalized reaction products.