Modern Synthetic Methods for Fluorine‐Substituted Target Molecules

Abstract

Fluorine has come to be recognized as a key element in materials science: in heat-transfer agents, liquid crystals, dyes, surfactants, plastics, elastomers, membranes, and other materials. Furthermore, many fluorine-containing biologically active agents are finding applications as pharmaceuticals and agrochemicals. Progress in synthetic fluorine chemistry has been critical to the development of these fields and has led to the invention of many novel fluorinated molecules as future drugs and materials. As a result of the electronic effects of fluorine substituents, fluorinated substrates and reagents often exhibit unusual and unique chemical properties, which often make them incompatible with established synthetic methods. Thus, the problem of how to control the unusual properties of compounds with fluorine substituents deserves much attention, so as to promote the design of facile, efficient, and environmentally benign methods for the synthesis of valuable organofluorine targets.

Studies on synthetic and structural characterization of new fluorine substituted phthalides of pharmaceutical interest

“…Aryl fluoride (Ar-F) moieties are synthetically useful functional groups broadly applicable in medicinal chemistry. They are isosteric to parent hydrocarbons and show improved lipophilicity as well as inertness to metabolic transformations [4][5][6] . Large number of fluorinated organic compounds exhibit antimicrobial 7,8 , antitumour and anti lung cancer 9 activities.…”

Stereoselective metal-free catalytic synthesis of chiral trifluoromethyl aryl and alkyl amines

“…2 Special attention has been recently devoted to the preparation of chiral molecules featuring stereocenters bearing directly a fluorine atom or a trifluoromethyl group. 3 Despite the great interest in the last years in the topic, the highly stereochemically efficient synthesis of chiral organofluorine compounds still represents a challenge for synthetic chemists. 4 Two approaches have been followed so far: in one case the direct introduction of a fluorine atom or a fluorinated residue is involved; 5 the second methodology, that has been preferred so far, is based on the stereoselective transformation of a fluorine-containing building block.…”

Fluorination methods in drug discovery

“…The rapid development of synthetic methodologies in organic fluorine chemistry 1n and the increased understanding of the impact of fluorination on biological properties 8 have made possible the design and synthesis of structurally-diverse and sophisticated drug candidates.…”