Recent Progress in the Selective Fluorinations of Some Functionalized Cycloalkenes
Melinda Nonn1, Csaba Paizs2, Loránd Kiss3
1MTA TTK Lendület Artificial Transporter Research Group, Institute of Materials and Environmental Chemistry, Research Center for Natural Sciences, Hungarian Academy of Sciences, Magyar Tudósok krt. 2, 1117, Budapest, Hungary.
Abstract:
Organofluorine compounds have had an increasing impact in synthetic organic chemistry and pharmaceutical research over the past two decades. Their syntheses and the development of novel synthetic approaches towards versatile fluorinated small molecules have received great interest. Our research team has designed various selective and stereocontrolled methods for the construction of fluorine-containing small molecular entities, involving the transformation of various functionalized cycloalkenes across their ring olefin bond. The synthetic methodologies developed to access various pharmacologically interesting fluorinated derivatives with multiple chiral centers might be valuable protocols for the preparation of other classes of organic compounds as well.
Related Concept Videos
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Cycloaddition Reactions: Overview
Limitations of Friedel–Crafts Reactions
Halogenation of Alkenes
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
Electrophilic Aromatic Substitution: Friedel–Crafts Alkylation of Benzene


