Synthetic Organofluorine Chemistry: Making, Breaking, and Using C-F Bonds
This presentation will be divided in two parts.
The first one will focus on the use of fluoride as a leaving group. Typically, fluoride has the worst leaving group ability of the halogen series in nucleophilic substitution reactions on alkyl halides. It is therefore not surprising that reactions involving the use of fluoride as a leaving group on a sp3 carbon are uncommon. I will present a series of synthetic transformations involving the use of a C(sp3)-F bond activation as a key step. In particular, approaches to monofluoroalkenes from 3,3-difluoropropenes via metal-catalyzed or conventional reactions will be presented. Nucleophilic substitution reactions of activated alkyl fluorides in aqueous solvent will also be discussed. Finally, we will examine the effect of stronger hydrogen-bond donor solvents on the reaction pathway. As such, reactions of benzylic fluorides in Friedel-Crafts reactions will be presented.
Understanding the interactions between lipid membranes and small molecules, peptides or proteins is of primary importance to determine their mechanism of action. In this context, solid-state NMR is a method of choice to study their effects on model membranes. Our goal involves marking, with a fluorine atom, phosphoglycerolipids to mimic eukaryotic and prokaryotic cell membranes. In this second part, the synthesis and characterization of monofluorinated dimyristoylphosphatidylcholine derivatives (F-DMPC) will be presented. Biophysical studies using infrared spectroscopy and solid-state NMR suggest that the incorporation of monofluorinated analogs of DMPC in model membranes does not significantly perturb the properties of the lipid bilayers.
Prof. Dr. Jean-François Paquin
Canada Research Chair in Organic and Medicinal Chemistry
Département de chimie,
FQRNT Center for Green Chemistry and Catalysis,
FQRNT Network for Research on Protein Function, Structure, and Engineering,
Université Laval, Québec, QC, CANADA G1V 0A6
For further information:
Prof. Dr. Gerd-Volker Röschenthaler
Professor of Chemistry
Focus Area: Health - Life Sciences & Chemistry
Building Research III, Room 86 / Campus Ring 6 / 28759 Bremen / Germany
Email: g.roeschenthaler [at] jacobs-university.de
Tel: +49 421 200-3138 / Fax: +49 421 200-3102
Link to Homepage: http://www.jacobs-university.de/ses/groeschenthaler