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.