Transition metal catalysis and nucleophilic fluorination
Charlotte Hollingworth1, Véronique Gouverneur
1Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, OX1 3TA, Oxford, UK.
This review highlights advances in transition metal-catalyzed nucleophilic fluorination for synthesizing valuable fluorinated compounds and pharmaceuticals. New fluoride reagents are enabling broader applications, including in Positron Emission Tomography (PET) imaging.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
- Radiochemistry
Background:
- Fluorinated compounds are crucial in pharmaceuticals and agrochemicals.
- Catalytic nucleophilic fluorination offers efficient synthesis routes.
- Positron Emission Tomography (PET) imaging relies on (18)F-radiochemistry.
Purpose of the Study:
- To review transition metal-catalyzed nucleophilic fluorination methods.
- To highlight the development of novel fluoride sources and reagents.
- To discuss applications in pharmaceutical synthesis and PET imaging.
Main Methods:
- Review of literature on transition metal-catalyzed fluorination reactions.
- Focus on nucleophilic fluorination of diverse substrates (aryl triflates, alkynes, allylic compounds, epoxides).
- Discussion of catalytic systems including Palladium and Iridium.
Main Results:
- Successful Pd(0)/Pd(II)-catalyzed synthesis of fluoroarenes from aryl triflates.
- Development of Tsuji-Trost allylic alkylation with fluoride.
- Advancements in catalytic asymmetric hydrofluorination of epoxides.
- Emergence of novel electrophilic fluorination reagents for late-stage functionalization.
Conclusions:
- Transition metal catalysis has significantly advanced nucleophilic fluorination.
- A wider array of nucleophilic fluoride sources is needed for broader applicability.
- New electrophilic fluorination reagents show promise for PET imaging and drug development.
More Related Videos
09:37Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
Published on: October 18, 2019
11:44Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
Published on: March 20, 2014
Related Concept Videos
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Properties of Organometallic Compounds
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Olefin Metathesis Polymerization: Overview
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists of a...
Heterogeneous Catalysis
Catalysis
