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4.4.39.1 Method 1: From Benzylic Hydrogens

DOI: 10.1055/sos-SD-004-00896

Bennetau, B.Science of Synthesis, (20024825.

As with aromatic rings, metalation of tolyl compounds, which is greatly facilitated by heteroatomic ortho substituents, provides a useful strategy for the introduction of trialkylsilyl groups at the benzylic position (Scheme 1). A great variety of benzylsilanes have been prepared by replacement of a benzylic hydrogen using alkyllithium reagents, often in the presence of a chelating amine, e.g. N,N,N,N-tetramethylethylenediamine.[‌1‌‌3‌]

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