Deoxyfluorination using Metal fluorides

Organofluorine compounds that contain a carbon-fluorine bond are used in a variety of applications, including pharmaceutical drugs to treat diseases, high-performance advanced materials, and agrochemicals for food supply to a growing population. The finite nature of many resources including the limited environmental tolerance towards our chemical industry requires transitioning towards more sustainable and safe chemistry. The linear route of production, in which scarce resources are consumed and their value-added products are degraded to waste, is a route cause of global crises such as climate change, diminished biodiversity, as well as food, water, and energy shortages. Within this context, innovation to produce fluorochemicals applying protocols that meet today's performance metrics, such as high performance, safety, and sustainability, is vital. In this context, our goal is to synthesize critically needed organofluorine compounds from safe and inexpensive metal alkali fluoride such as potassium fluoride. Specifically, this proposal aims at inventing a new reaction to convert readily available alcohols into fluorochemicals using potassium fluoride instead of commonly used deoxyfluorination reagents [e.g. diethylaminosulfur trifluoride] that are derived from SF4, a hazardous chemical itself prepared from the dangerous chemical hydrogen fluoride. Our current approach is based on the Gouverneur group's previous studies on the new concept of "Hydrogen Bonding Phase Transfer Catalysis" for the activation of alkali metal fluorides with a hydrogen bond donor urea catalyst. Specifically, we propose a dual activation process for both the alcohol and potassium fluoride to convert readily available racemic alcohols into enantioenriched fluorinated motifs that are of importance for a pharmaceutical drug.