Dehalogenative and Deprotonative Lithiation of Pyridines: A Second Wind for Trimethylsilylmethylithium (TMSCH2Li)

Author(s): Philippe C. Gros, Yves Fort

Journal Name: Current Organic Chemistry

Volume 15 , Issue 14 , 2011


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Abstract:

Trimethylsilylmethyllithium (TMSCH2Li) is well-known as a nucleophilic reagent in methylation and methylenation reactions but its application in deprotonation or halogen-metal exchange has been underexploited to date. The present review covers new applications of TMSCH2Li and TMSCH2Li-LiDMAE (LiDMAE=Lithium 2-dimethylamino ethoxide) in selective metallation of pyridine derivatives focusing on the design of more applicable bromine-lithium exchange and deprotonation processes as well as new selectivities.

Keywords: Trimethylsilylmethyllithium, aggregates, functionalisation, lithiation, nucleophilicity, pyridine, selectivity, TMEDA, PMDETA, DIA (diisopropylamine), Fluoropyridines, Lithiation of (S)-Nicotine, halogen-metal exchange, deprotonation

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Article Details

VOLUME: 15
ISSUE: 14
Year: 2011
Page: [2329 - 2339]
Pages: 11
DOI: 10.2174/138527211796150624
Price: $58

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