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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
TBADT-Photocatalyzed Trifluoromethylation of Phenylpropiolamides Using Langlois Reagent: Access to Oxindole
Punith S Gowda1, Jagadeesh Reddy Thondur1, Duddu S Sharada2
1Department of Chemistry, Indian Institute of Technology Hyderabad, Kandi, Sangareddy, Telangana 502284, India.
Abstract:
In this study, we report the radical-mediated trifluoromethylation of phenylpropiolamides using the Langlois reagent (CF3SO2Na) under ultraviolet light irradiation, with tetrabutylammonium decatungstate (TBADT) serving as an efficient inorganic photocatalyst. This method synthesizes a wide range of oxindoles by generating a CF3 radical, which induces an intermolecular C-CF3 bond (via a Michael addition on the propiolamide moiety), followed by an intramolecular C-C bond formation and reduction sequence. Thus, a broad range of trifluoromethyl-substituted oxindoles have been accomplished in high yields under mild conditions.
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