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
Call for Papers in Thematic Issues
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
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