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
Current Organic Chemistry
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.
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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
DOI https://dx.doi.org/10.2174/138527211796150624 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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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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