Synthesis and reactivity of α‐cumyl bromodifluoromethanesulfenate: application to the radiosynthesis of [18F]arylSCF3

Wu J, Zhao Q, Wilson TC, Verhoog S, Gouverneur V, Lu L, Shen Q

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.

Keywords:

positron emmision tomography

,

trifluoromethylthio

,

electrophilic

,

bromodifluoromethylthio

,

fluorine