Dual co/photoredox catalysis for the synthesis of fluorine-containing skipped dienes featuring a quaternary carbon stereocenter
Fluorine-containing functional groups have become of crucial importance for medicinal and agrochemical applications. The incorporation of these moieties into molecular structures allows for significant opportunities to take advantage of bioisosterism as well as to fine-tune the chemical or pharmacological properties of a desired molecule. The objective of the FUSE project is to pioneer a novel approach for the preparation of fluorinated and chiral skipped dienes bearing a quaternary carbon stereocenter. Developing methodologies for these elusive compounds allows for a wide range of synthetic post-transformations and they thus serve as valuable building blocks in synthetic chemistry and pharmaceutical development programs. The project will expand the chemical space of hydrofluoroolefins (HFOs) and utilize these fourth-generation refrigerants as readily available and inexpensive starting materials. To achieve the challenging targets, a mild, visible-light photoredox based dual catalytic approach is utilized using earth-abundant (cobalt) first-row transitional metal catalysis. As such, the replacement of the typically hazardous metal reagents utilized in the state of the art and minimizing chemical waste is forecasted. The proposed programme will be carried out in close cooperation with an industrial partner in order to provide a new flow strategy for constructing these skipped fluorodiene scaffolds. This ambitious and innovative project will contribute to propagate the sustainability and reinforce the application potential of HFOs for academic and industrial applications. The project merges multidisciplinary aspects with intersectorial knowledge transfer, enabling the transition to more sustainable development in the fine chemical and pharmaceutical sector.