Generic placeholder image

Current Organic Chemistry

Editor-in-Chief

ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

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

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

Volume 15, Issue 14, 2011

Page: [2329 - 2339] Pages: 11

DOI: 10.2174/138527211796150624

Price: $65

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


Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy