Organofluorine compounds have gained increasing interest in the fields of materials science, medicinal chemistry and agrochemical development. Accordingly, deoxofluorination stands as a key transformation in the organic chemist’s toolbox, enabling easy access to organofluorine compounds. Hitherto, the vast majority of available reagents to conduct this transformation are sulfur-based reagents (SF<sub>4</sub>, DAST, Deoxofluor, XtalFluorE, etc.) However, practical application of many of these reagents has been hampered due to cost, toxicity, environmental pollution, thermal instability and/or drastic reaction conditions.<br/><br/>Owing to their superior stability and distinct reactivity, when compared to other acyl halides, acyl fluorides are versatile intermediates in organic synthesis. Given their importance, we developed a streamlined process for their preparation directly from carboxylic acids using a phosphine-based reagent system. In this protocol, a combination of inexpensive and readily available commodity chemicals and fluoride ion are used to effect the transformation. Scope, limitations and the application of this process in the synthesis of biologically relevant compounds will be presented.

Phosphine-based reagent system for deoxofluorination

256th National Meeting (2018)

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