Tetrahedron p. 4471 - 4478 (2019)
Update date:2022-08-02
Topics: Visible-Light Mediated Trifluoromethylation p-Quinone Methides 1,6-Conjugate Addition Pyrylium Salt
Ghosh, Krishna Gopal
Chandu, Palasetty
Mondal, Santanu
Sureshkumar, Devarajulu
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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