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Reprogramming Conformation by Fluorination: Exploring New Areas of Chemical Space

Project description

Strategic fluorination could unlock tremendous chemical potential

Organofluorine compounds, organic molecules containing carbon-fluorine bonds, are widely used to make high-impact pharmaceuticals, imaging agents, agrochemicals and various materials. Numerous pharmaceuticals are fluorinated to impart enhanced metabolic and oxidative stability, lipophilicity and membrane permeability. However, we have likely only seen the tip of the iceberg when it comes to the potential of organofluorine compounds. The roadblock has been limitations in controlling fluorination sites and the resulting 2D and 3D molecular architecture. RECON is working to unlock the potential of complex fluorinated compounds with rational design of structure for highly specific and unique function. Even better, these methods rely on cost-effective and commercially available fluoride feedstock.

Objective

Despite the abundance of organic compounds in Nature, only 12 contain fluorine. In contrast, fluorinated organic materials account for over 40% of all pharmaceuticals and agrochemicals. Closer inspection of the fluorination patterns in these functional molecules reveals striking extremes towards perfluorination (in both 2D and 3D scaffolds) or single site fluorination predominantly in aryl substituents. Consequently, most fluorinated moieties in functional materials lack stereochemical information and are thus achiral. This disparity between the paucity of naturally occurring organofluorine compounds and their venerable history in functional molecule design confirms the enormous potential of fluorinated materials in the discovery of novel properties. That progress has largely been confined to 3 dimensional achiral and 2 dimensional achiral architectures reflects the synthetic challenges associated with preparing stereochemical defined multiply fluorinated systems. A major limitation in the construction of C(sp3)-F units remains the need for substrate pre-functionalisation via oxidation and the competing substitution/elimination scenario that compromises efficiency in the deoxyfluorination. This problem is magnified in the synthesis of optically active fluorides where the deoxyfluorination can compromise the enantiopurity of the starting materials. The principle aim of RECON is to facilitate exploration of 3D, chiral space by providing access to multiply fluorinated, stereochemically complex organofluorine materials from simple feedstock using inexpensive, commercially available fluoride sources. In providing a modular platform to rationally place function on a structural basis, exploration of uncharted chemical space will accelerate the discovery of next generation materials for medicinal and agrochemistry, material sciences and bio-medicine.

Host institution

UNIVERSITAET MUENSTER
Net EU contribution
€ 1 999 375,00
Address
SCHLOSSPLATZ 2
48149 MUENSTER
Germany

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Region
Nordrhein-Westfalen Münster Münster, Kreisfreie Stadt
Activity type
Higher or Secondary Education Establishments
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Total cost
€ 1 999 375,00

Beneficiaries (1)