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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 [18 F]KF/K222  , a process giving access to [18 F]arylSCF3 in two steps from the corresponding aryl boronic pinacol esters.

Original publication

DOI

10.1002/anie.201813708

Type

Journal article

Journal

Angew Chem Int Ed Engl

Publication Date

18/02/2019

Volume

58

Pages

2413 - 2417

Keywords

PET, boron reagents, bromodifluoromethylthiolation, fluorine, radiolabeling