Carbon‐to‐Carbon Anion Relay Chemistry: Facile Generation of Substituted Allyllithium Species | Zendy

Zheng Pinguan | Zendy; Cai Zhengxin | Zendy; Garimallaprabhakaran Aswinkumar | Zendy; Rooshenas Parham | Zendy; Schreiner Peter R. | Zendy; Harmata Michael | Zendy

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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.

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