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

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

Volume: 15 Issue: 14

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

Affiliation:

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

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.

Cite this article as:

C. Gros Philippe and Fort Yves, Dehalogenative and Deprotonative Lithiation of Pyridines: A Second Wind for Trimethylsilylmethylithium (TMSCH2Li), Current Organic Chemistry 2011; 15 (14) . https://dx.doi.org/10.2174/138527211796150624