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. 2011 Jan 26;133(3):409-11.
doi: 10.1021/ja1096732. Epub 2010 Dec 16.

Palladium-catalyzed allylic C-OH functionalization for efficient synthesis of functionalized allylsilanes

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Palladium-catalyzed allylic C-OH functionalization for efficient synthesis of functionalized allylsilanes

Nicklas Selander et al. J Am Chem Soc. .

Abstract

A new method is described for palladium-catalyzed allylic silylation using allylic alcohols and disilanes as precursors. The reactions proceed smoothly under mild and neutral conditions, and this method is suitable for synthesis of regio- and stereodefined allylsilanes. The presented silylation reaction can be easily extended to include synthesis of allylboronates by change of the dimetallic reagent. The presented synthetic procedure offers a broad platform for the selective synthesis of functionalized allyl metal reagents, which are useful precursors in advanced organic chemistry and natural product synthesis.

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