Carbon-to-Carbon Anion Relay Chemistry: Facile Generation of Substituted Allyllithium Species.

Treatment of [2-(2-bromophenyl)allyl]trimethylsilane with tBuLi in THF at –78 °C resulted in the rapid migration of the trimethylsilyl group to afford an allylic organolithium that can be easily trapped by a wide range of electrophiles. This is a rare example of a synthetically useful and efficientcarbon-to-carbon migration of a silicon group and represents a new approach to allylic organolithium species using anion relay chemistry.