Design of Modern Approaches for the (Asymmetric) Synthesis of Original Fluorinated Molecules

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This collaborative project aims at developing novel and modern approaches towards the synthesis of unprecedented fluorinated molecules. Fluorinated motifs are important in organic chemistry, namely in agrochemical and pharmaceutical active ingredients. Indeed, the targeted compounds substituted with emergent fluorinated groups will allow for new advances in the field by expanding considerably the chemical space of fluorinated molecules as so far this is an uncharted research area. To reach that challenging goal, two complementary approaches based on photocatalysis (WP1) and asymmetric anion-binding (WP2) strategies are envisioned. For both approaches, the design and synthesis of innovative neutral and cationic mono-/difluoromethylating and difluoromethylthiolating reagents will be carried out, providing the required platform for the later implementation in the catalytic methods to be developed. Hence, in WP1 the selective functionalization of benzylic C(sp3)-H bonds with difluoromethylating and difluoromethylthiolating sources will be pursued. Alternatively, in WP2 enantioselective fluoromethylation, difluoromethylation and difluoromethylthiolation methods using different pro-chiral nucleophiles, embracing a catalytic anion-binding activation of electrophilic cationic reagents, will be developed. The combination of the expertise in organofluorine chemistry (Besset, synthetic methodologies and design of original reagents) and photo- or organocatalysis (García Mancheño, organophotocatalysts design and anion-binding methodologies) is essential in tackling this challenging venture. The success of the AsymFluoChem project will enrich the chemist’s toolbox with methods allowing the synthesis of unprecedented both non-chiral and enantioenriched molecules using modern technologies. Furthermore, novel perspectives in organofluorine chemistry, organocatalysis and photochemistry will be developed, which are of great interest in academia and for chemical industry applications.