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Carbon‐to‐Carbon Anion Relay Chemistry: Facile Generation of Substituted Allyllithium Species
Author(s) -
Zheng Pinguan,
Cai Zhengxin,
Garimallaprabhakaran Aswinkumar,
Rooshenas Parham,
Schreiner Peter R.,
Harmata Michael
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100783
Subject(s) - chemistry , allylic rearrangement , trimethylsilane , trimethylsilyl , electrophile , carbon fibers , ion , combinatorial chemistry , silicon , organic chemistry , medicinal chemistry , catalysis , materials science , composite number , composite material
Treatment of [2‐(2‐bromophenyl)allyl]trimethylsilane with t BuLi 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.