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Please login or sign up for a free trial to access the full content. 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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Me MM8Me MeMe, MMM, 8°M 88 [‌88‌]
MM MMeMe8 MMM, MMMMM, MMM, 88°M 88 [‌88‌]
Me Me MMM, MMM, 88°M 88 [‌88‌]
MMe MeMe MMM, MMM, 88°M 88 [‌88‌]
MM M (eeeee eeeee) e-MeMe, MMM, 88°M, 88 [‌88‌]
Me M (eeeeeeeeeeeee) e-MeMe, MMMMM, M8M88, 88°M 88 [‌88‌]
M M (eeeeeeee) MeMe, MMM, 88°M 88 [‌88‌]

Meeeeeeeeeee Meeeeeeee

8-[(Meeeeeeeeeeeee)eeeeee]eeeeeee eeee (8); Meeeeee Meeeeeeee:[‌8‌]

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