Cation Radical-Accelerated Nucleophilic Aromatic Substitution for Amination of Alkoxyarenes

Modern Nucleophilic Aromatic Substitution

Synthesis of polynitroxides based on nucleophilic aromatic substitution.

The scope and limitations of the synthesis of polynitroxides by nucleophilic substitution of electron-deficient fluorinated aromatic compounds are described. The method provides a facile route to the formation of polynitroxides exhibiting strong electron exchange between nitroxide groups.

Transetherification of 2,4-dimethoxynitrobenzene by aromatic nucleophilic substitution

In view of the few reports concerning aromatic nucleophilic substitution reactions featuring an alkoxy group as a leaving group, the aromatic nucleophilic substitution of 2,4-dimethoxynitrobenzene was investigated with a bulky t-butoxide nucleophile under microwave irradiation. The transetherification of 2,4-dimethoxynitrobenezene with sodium t-butoxide under specific conditions, namely for 20 ...

On the frontier between nucleophilic aromatic substitution and catalysis.

A study on the arylation of heteroatom nucleophiles by using activated haloarenes, with or without metal catalysts, is reported. A discussion concerning the involvement of traces of metals is presented, supported by an unexpected ''ligand'' effect in the absence of added metal catalysts. We believe that the frontier between nucleophilic aromatic substitution and catalysis will likely prove to b...

TRIPHENYLPHOSPHINE CATALYZED AROMATIC ELECTROPHILIC SUBSTITUTION OF 2-HYDROXYACETOPHENONE MEDIATED BY VINYLTRIPHENYLPHOSPHONIUM CATION

Protonation of the highly reactive 1:l intermediate produced in the reaction between triphenylphosphine and dimethyl acetylenedicarboxylate by 2- hydroxyacetophenone leads to vinyltriphenylphosphonium salt, which undergoes aromatic electrophilic substitution reaction with the conjugate base to produce compounds 4,5, and 6 in 1 : 1.2:0.5 ratios