Depending on the selected DFT functional, two different mechanisms are found for two organic reactions (an intramolecular nucleophilic aromatic substitution and a nucleophilic addition on a carbonyl moiety). Indeed, B3LYP predicts a concerted mechanism whereas M06-2X foresees a multistep one. Calculations at the MP4(SDQ) level proved the mechanisms to be stepwise. We studied these reactions wit...

A straightforward synthetic route to arylazoindazoles via nucleophilic aromatic substitution is presented. Upon deprotonation of the NH group, a C6F5-substituted formazan undergoes facile cyclization as a result of intermolecular nucleophilic substitution (SNAr). This new class of azo photoswitches containing an indazole five-membered heterocycle shows photochemical isomerization with high fati...

Particular and rare examples of aromatic nucleophilic substitution are described as tele-substitution. Usually strong nucleophiles are involved and the entering group is introduced at a position distant from the expected leaving group. Examples of tele-substitution in various heteroaromatic systems are presented.

The N-arylindole subunit is an important species in many biologically active and pharmaceutically important compounds, which display antiestrogen [1], analgesic [2], antiallergy [3], antimicrobial [4], and neuroleptic activity [5]. Although the traditional coppercatalyzed coupling of an aryl halide with a heteroatombased nucleophile, the Ullmann-type coupling reaction, has remained a standard m...

The title compound was synthesized in near-quantitative yield using nucleophilic aromatic substitution of 4,4′-(hexafluoroisopropylidene)diphenol (BPAF) with perfluoropyridine (PFP). purity and structure were determined by NMR (1H, 13C, 19F), GC–EIMS, single-crystal X-ray crystallography.

Figure 1: Directed aromatic functionalization methods. The title of this Thematic Series brings to the minds of most organic chemists the beautifully logical aromatic electrophilic substitution (SEAr) [1-5] and, to a lesser extent, nucleophilic aromatic substitution (SNAr) [2,6,7] reactions as taught to many generations of students in their first organic chemistry courses [8] (Figure 1). Being ...

The nitro group of methyl 3-nitropyridine-4-carboxylate (1) has successfully been replaced by fluoride anion via nucleophilic aromatic substitution to give the 3-fluoro- pyridine-4-carboxylate 2.

A novel method for the synthesis of pyrazolo[1,5-a]quinolines under the transition-metal-free conditions has been developed. This method involves a novel combination of aromatic nucleophilic substitution and Knoevenagel condensation reactions to give pyrazolo[1,5-a]quinolines.

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.