Lateral lithiation in deep eutectic solvents: regioselective functionalization of substituted toluene derivatives

The heteroatom-directed lateral lithiation of functionalized toluenes in a choline chloride-based eutectic mixture is reported. The metalations proceed within ultrafast reaction times, with a broad substrate and electrophile scope. The directing groups provide a rapid and high regioselective access...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2020-02, Vol.56 (16), p.2391-2394
Main Authors: Arnodo, Davide, Ghinato, Simone, Nejrotti, Stefano, Blangetti, Marco, Prandi, Cristina
Format: Article
Language:English
Subjects:
Choline
Derivatives
Regioselectivity
Substrates
Toluene
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Summary:The heteroatom-directed lateral lithiation of functionalized toluenes in a choline chloride-based eutectic mixture is reported. The metalations proceed within ultrafast reaction times, with a broad substrate and electrophile scope. The directing groups provide a rapid and high regioselective access to functionalized aromatic derivatives of remarkable synthetic value. Ultrafast heteroatom-directed lateral lithiation of substituted toluene derivatives using choline chloride-based eutectic mixtures as bio-inspired sustainable reaction media.
ISSN:1359-7345
1364-548X
DOI:10.1039/d0cc00593b