Visible-light mediated trifluoromethylation of p-quinone methides by 1,6-conjugate addition using pyrylium salt as organic photocatalyst |
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| Authors: | Krishna Gopal Ghosh Palasetty Chandu Santanu Mondal Devarajulu Sureshkumar |
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| Institution: | 1. Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata Mohanpur, 741246, West Bengal, India;2. Okinawa Institute of Science and Technology (OIST), 1919-1, Tancha, Onna-son, Okinawa, Japan |
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| Abstract: | A transition metal free visible light mediated organo photoredox catalyzed trifluoromethylation of p-quinone methides (p-QMs) to construct fluoro-analogs of dichlorodiphenyltrichloroethane (DDT) is reported using a bench stable, inexpensive Langlois reagent as a trifluoromethyl radical source. This protocol could generate a benzylic C(sp3)-CF3 bond with excellent yield under mild reaction conditions using 1,6-conjugate addition/aromatization of trifluoromethyl radical in the absence of any external additives. Further, we demonstrate di-trifluoromethylation and gram scale synthesis of this reaction. |
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| Keywords: | Corresponding author Trifloromethylation Photoredox catalysis 1 6-Conjugate addition Organocatalysis |
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