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Aryl imidazylates and aryl sulfates. Novel electrophiles in metal-free ArSN1 reactions

Authors: 
Hisham Qrareya, Stefano Protti, and Maurizio Fagnoni.
Journal Name: 
Journal of Organic Chemistry (JOC).
Volume: 
79
Issue: 
3
Pages From: 
11527
To: 
11533
Date: 
Thursday, October 30, 2014
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.