The sulfonyl fluoride functional group is one that has widespread utility across a number of different areas of chemistry. For example, sulfonyl fluoride-based molecules make excellent biological probes that have been successfully applied to a number of targets, yet the moiety is versatile enough that it is also at the forefront of a novel type of “SuFEx” click reaction, enabling novel polymerization approaches. The underlying property driving these methods is strength of the S-F bond in certain circumstances, such as stability to hydrolysis under physiological conditions, and its reactivity under others, such as in the presence of silicon-based functional groups; an almost unique combination of characteristics with many potential applications. Despite this clear utility, methods of making sulfonyl fluorides are mostly restricted to the historical approach via the corresponding sulfonyl chloride using potassium bifluoride. This is itself usually synthesized through an archaic route using chlorosulfonic acid, and both these methods require the use of harsh reagents suffering from poor functional group compatibility. The Willis Group at the University of Oxford have a special interest in the chemistry of sulfur, and in particular late-stage methods to install sulfur-based functional groups, focusing on utility and substrate tolerance. With these objectives in mind, we set about using the DABSO sulfur dioxide surrogate developed within our laboratory to devise an approach to sulfonyl fluorides which could overcome the issues with previous synthetic routes. In this poster we present the results of this work, showing how we have managed to achieve a facile, one-pot palladium-catalyzed synthesis of sulfonyl fluorides from readily available aryl bromides which can be applied to a vast array of substrates, including active pharmaceutical ingredients.

One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides

256th National Meeting (2018)

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