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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.