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Synthesis and Reactivity of α‐Cumyl Bromodifluoromethanesulfenate: Application to the Radiosynthesis of [ 18 F]ArylSCF 3
Author(s) -
Wu Jiang,
Zhao Qunchao,
Wilson Thomas C.,
Verhoog Stefan,
Lu Long,
Gouverneur Véronique,
Shen Qilong
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201813708
Subject(s) - chemistry , pinacol , aryl , reagent , electrophile , halogen , reactivity (psychology) , catalysis , boron , halide , combinatorial chemistry , medicinal chemistry , organic chemistry , medicine , alternative medicine , pathology , alkyl
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/K 222 , a process giving access to [ 18 F]arylSCF 3 in two steps from the corresponding aryl boronic pinacol esters.