"The number of active ingredients in the pharmaceutical industry, the health sector and modern crop protection that contain a benzylic fluoride or a fluorine substituent directly adjacent to a heteroaryl motif is significant and extrapolation of current trend indicates a definite growth to be expected through the 21st century. Many of these biologically important compounds with the fluorine substituent on a stereogenic centre targets must be made available enantiopure. This includes compounds that are labelled with 18F, the positron emitting radionuclide of choice for Positron Emission Tomography (PET).Despite the importance of these fluorinated target motifs, only few synthetic methodologies are reported in literature, most of them with limitations in terms of scope and selectivity.Transition metal catalysed processes are ideally suited for a mild and selective C-F bond formation but are still very rare, in part due to the fact that C-F reductive elimination is a notoriously difficult transformation. In this context, last year, Gouverneur et al. reported the first palladium-catalysed allylic fluorination, which has been proved to be feasible for 18F labelling. Doyle reported a stereocontrolled variant of this transformation. On the basis of these exciting results, this proposal offers to develop a new approach for the stereoselective preparation of a broad range of benzylic fluorides inclusive of enantiopure derivatives; the strategy is based on a transition metal catalysed C(sp3)-F bond cleaving or bond forming process."