Synthesis and Reactivity of α‐Cumyl Bromodifluoromethanesulfenate: Application to the Radiosynthesis of [18F]ArylSCF3

On the radio: A highly reactive electrophilic bromodifluoromethylthiolating reagent, α‐cumyl bromodifluoromethanesulfenate, was developed and coupled with a range of (hetero)aryl boronic pinacol esters under copper catalysis. The resulting bromodifluoromethylthiolated (hetero)arenes were amenable to halogen exchange using [¹⁸F]KF/K₂₂₂. This is the first radiosynthetic route to [¹⁸F]arylSCF₃ via (hetero)aryl–SCF₃ bond construction.

Abstract

A highly reactive electrophilic bromodifluoromethylthiolating reagent, α‐cumyl bromodifluoro‐methanesulfenate 1, was prepared to allow for direct bromodifluoromethylthiolation of aryl boron reagents. This coupling reaction takes place under copper catalysis, and affords a large range of bromodifluoromethylthiolated arenes. These compounds are amenable to various transformations including halogen exchange with [¹⁸F]KF/K₂₂₂ , a process giving access to [¹⁸F]arylSCF₃ in two steps from the corresponding aryl boronic pinacol esters.

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