Transition Metal Free Nucleophilic Benzylation of Nitroarenes. Umpolung of the Friedel Crafts Reaction
Advanced Synthesis and Catalysis（2019）
Abstract
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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Key words
Aromatic substitution,Benzylation,Nucleophilic substitution,Umpolung,VNS
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