Polyfluoroarene-Capped Thiophene Derivatives via Fluoride-Catalyzed Nucleophilic Aromatic Substitution

Modern Nucleophilic Aromatic Substitution

Synthesis of 3-aminoBODIPY dyes via copper-catalyzed vicarious nucleophilic substitution of 2-halogeno derivatives.

2-Halogeno BODIPYs undergo copper catalysed nucleophilic substitution with alkyl amines and anilines and an amide to give the corresponding 3-aminoBODIPY derivatives. The substrates are readily prepared by the regioselective 2-halogenation of the chemically robust, preformed BODIPYs thus providing an alternative to direct nucleophilic substitution of the corresponding 3-halogenoBODIPYs which re...

Synthesis of new cytotoxic aminoanthraquinone derivatives via nucleophilic substitution reactions.

Aminoanthraquinones were successfully synthesized via two reaction steps. 1,4-Dihydroxyanthraquinone (1) was first subjected to methylation, reduction and acylation to give an excellent yield of anthracene-1,4-dione (3), 1,4-dimethoxyanthracene-9,10-dione (5) and 9,10-dioxo-9,10-dihydroanthracene-1,4-diyl diacetate (7). Treatment of 1, 3, 5 and 7 with BuNH2 in the presence of PhI(OAc)2 as catal...

A QM/MM study of a nucleophilic aromatic substitution reaction catalyzed by 4-chlorobenzoyl-CoA dehalogenase.

Calculated using a QM/MM method, the free energy profile for the conversion of 4-chlorobenzoate to 4-hydroxybenzoate catalyzed by 4-chlorobenzoyl-CoA dehalogenase indicates the existence of a stable Meisenheimer complex.

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.