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Synfacts 2007(2): 0203-0203  
DOI: 10.1055/s-2006-955801
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Phosphazene Base Promoted Functionalization of Aryltrimethylsilanes

Contributor(s): Paul Knochel, Andrei Gavryushin
K. Suzava, M. Ueno, A. E. H. Wheatley, Y. Kondo*
Tohoku University, Sendai, Japan and University of Cambridge, UK
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Publication History

Publication Date:
23 January 2007 (online)

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Significance

This publication describes an elegant method for the generation of an aryl anion, using aryltrimethylsilanes and a strong organic phosphazene base. In some cases, this method can be advantageously used for the conversion of aryl- or alkenyltrimethylsilanes, including functionalized ones, into the corresponding benzylic alcohols. This is an interesting example of a catalytic base-induced desilylation reaction of arenes which occurs instead of the usual deprotonation.