Transition Metal Free Nucleophilic Benzylation of Nitroarenes. Umpolung of the Friedel Crafts Reaction | Zendy

Kisiel Kacper | Zendy; Brześkiewicz Jakub | Zendy; Loska Rafał | Zendy; Mąkosza Mieczysław | Zendy

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Transition Metal Free Nucleophilic Benzylation of Nitroarenes. Umpolung of the Friedel Crafts Reaction

Author(s) -

Kisiel Kacper,

Brześkiewicz Jakub,

Loska Rafał,

Mąkosza Mieczysław

Publication year - 2019

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.201801715

Subject(s) - chemistry , umpolung , deprotonation , counterion , friedel–crafts reaction , nucleophile , transition metal , benzyl chloride , selectivity , organic chemistry , chloride , medicinal chemistry , catalysis , combinatorial chemistry , polymer chemistry , ion

Benzyl chloride and its derivatives are efficiently deprotonated with strong bases to form α ‐chlorocarbanions. These anions are long‐lived enough to enter VNS reactions with nitroarenes or nitroheteroarenes to give a variety of unsymmetrical o ‐ and p ‐nitrodiarylmethanes. Selectivity of the reaction can be controlled to some extent by changing metal counterions of the base.

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