Authors
Hisham Qrareya
Stefano Protti
and Maurizio Fagnoni.
Pages From
11527
Pages To
11533
Journal Name
Journal of Organic Chemistry (JOC).
Volume
79
Issue
3
Keywords
ArSN1 reaction, metal-free arylation.
Project
the Fondazione Cariplo (Grant 2012-0186). S.P
Abstract

Some oxygen-bonded substituents were investigated as leaving groups in photoinduced ArSN1 reactions. Irradiation of aryl imidazylates and of the corresponding imidazolium salts mainly caused homolysis of the ArO−S bond. However, previously unexplored trifluoroethoxy aryl sulfates were found to undergo efficient metal-free arylation. The sulfates were conveniently generated in situ by dissolving the corresponding imidazolium salts in basic 2,2,2-trifluoroethanol.