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

Journal article

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.

Authors: Wu, J; Zhao, Q; Wilson, TC; Verhoog, S; Gouverneur, V

• Publication status: Published
• Peer review status: Peer reviewed
• Publisher: Wiley
• Journal: Angewandte Chemie (International ed. in English)
• Volume: 58
• Issue: 8
• Pages: 2413-2417
• Publication date: 2019-01-25
• Acceptance date: 2018-12-17
• DOI: 10.1002/anie.201813708
• EISSN: 1521-3773
• ISSN: 1433-7851
• Pmid: 30575245
• Language: English
• Keywords: electrophilic; bromodifluoromethylthio; positron emmision tomography; fluorine; trifluoromethylthio