Descripción del proyecto
La fluoración estratégica podría tener un potencial químico enorme
Los compuestos organofluorados, moléculas orgánicas que contienen enlaces carbono-flúor, son ampliamente usados para fabricar productos farmacéuticos de gran impacto, agentes de imagen, productos agroquímicos y diversos materiales. Muchos productos farmacéuticos son fluorados con el fin de conferirles estabilidad metabólica y oxidativa mejorada, lipofilia y permeabilidad de la membrana. Sin embargo, probablemente tan solo hemos visto la punta del iceberg por lo que refiere al potencial de los compuestos organofluorados. El obstáculo han sido las limitaciones en el control de los sitios de fluoración y la arquitectura molecular en 2D y 3D resultante. RECON está trabajando para desarrollar el potencial de los compuestos fluorados complejos con el diseño racional de una estructura que permita conseguir una función única sumamente específica. Mejor aún, estos métodos se basan en materias primas económicas disponibles comercialmente.
Objetivo
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.
Ámbito científico
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Régimen de financiación
ERC-COG - Consolidator GrantInstitución de acogida
48149 MUENSTER
Alemania