A unique 1,4-silyl group migration from carbon to carbon: Formation of benzylic silane in the reaction of sterically hindered benzylic telluride with alkyllithium

The reaction of sterically hindered benzylic telluride bearing 2,4,6-tris[bis(trimethylsilyl)methyl]phenyl (Tbt) group with 2.0 eq. of n-BuLi and HSi(OMe)3 afforded a 1,4-silicon rearrangement product. This rearrangement is made possible by the intermediacy of a 5-membered silicate. The product may be exploited as a potential motif for the synthesis of numerous multiply bonded systems containing heavier group 14 elements.