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Isolation and characterization of a lithiated pyridine – aggregation in the solid state and in solution

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Abstract

Pyridyllithiums are ubiquitous intermediates used for the electrophilic functionalization of pyridines. In this work, the isolation of a pyridyllithium is reported. Single crystal XRD revealed a dimer in the solid state. In THF solution it was identified as a monomer using DOSY NMR spectroscopy. Calculations showed that the pyridyllithium is a very electron rich pyridine superbase, which may account for its high reactivity.

Graphical abstract: Isolation and characterization of a lithiated pyridine – aggregation in the solid state and in solution

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Submitted
20 Feb 2020
Accepted
16 Mar 2020
First published
18 Mar 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Isolation and characterization of a lithiated pyridine – aggregation in the solid state and in solution

N. M. C. Schmidlin, H. Scherer, A. Hoffmann and T. Böttcher, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC01355B

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