595548-71-3

Usage

Class

Indoline

Contains

Fluorophenyl group

Derived from

Indoline (a bicyclic heterocycle containing a six-membered benzene ring fused to a five-membered nitrogen-containing ring)

Potential pharmacological properties

Studied for its potential in medicinal chemistry

Possible applications

Drug development, building block for the synthesis of other compounds

Utility in material science

Due to its fluorinated structure

Use as reference standard

For analytical chemistry purposes

Upstream product

• 782-17-2 2-(4-fluorophenyl)indole 

Downstream Products

• 1143570-98-2 (-)-(S)-2-(4-fluorophenyl)indoline 

Relevant academic research and scientific papers

Kinetic resolution of indolines through reductive amination of aldehydes by chiral Br?nsted acid

We have developed a highly efficient and practical strategy for the kinetic resolution of indoline derivatives, involving a chiral Br?nsted acid-catalyzed iminium ion formation and asymmetric transfer hydrogenation cascade process. The kinetic resolution allows the synthesis of 2-substituted N-benzylindolines in good yields with moderate to excellent enantioselectivities.

Chiral Phosphoric Acid Catalyzed Kinetic Resolution of Indolines Based on a Self-Redox Reaction

A strategy for oxidative kinetic resolution of racemic indolines was developed, employing salicylaldehyde derivative as the pre-resolving reagent and chiral phosphoric acid as the catalyst. The iminium intermediate, formed by the condensation reaction of an enantiomer of indoline with salicylaldehyde derivative, was hydrogenated by the same enantiomer of indoline to afford another enantiomer of indoline by a self-redox mechanism. The oxidative kinetic resolution of 2-aryl-substituted indolines proceeded to give enantiomers in good yields with excellent enantioselectivities.

Chiral phosphoric acid-catalyzed oxidative kinetic resolution of indolines based on transfer hydrogenation to imines

The oxidative kinetic resolution of 2-substituted indoline derivatives was achieved by hydrogen transfer to imines by means of a chiral phosphoric acid catalyst. The oxidative kinetic resolution was applicable to racemic alkyl- or aryl-substituted indolines, and the remaining indolines were obtained in good yields with excellent enantioselectivities.

Kinetic resolution of indolines by Pd-catalyzed asymmetric ally Lie amination

The kinetic resolution of indolines was realized via a Pd-catalyzed allylic substitution reaction by using Trost's chiral ligand L10, affording optically active indolines and N-allylated indolines in high yields and high enantioselectivities with an 5 factor up to 59, which provided the first example for the kinetic resolution of nucleophiles via a transition-metal-catalyzed allylic substitution reaction. 2009 American Chemical Society.