Introduction of Trifluoroethylamine as Amide Isostere by C–H Functionalization of Heteroarenes

Abstract : A direct and efficient introduction of a trifluoroethylamine motif into various heteroaromatic structures, using a readily available xanthate S-[1-(N-acetylamino)-2,2,2-trifluoroethyl]-O-ethyl dithiocarbonate (5), is reported. Medicinally relevant trifluoroethylaminated heteroarenes containing a wide range of functional groups were successfully synthesized under mild conditions. This amide isostere could be introduced into both electron-rich and -poor heteroarenes to give the desired products in one step. The beneficial effect of camphorsulfonic acid (CSA) was also demonstrated with electron-deficient heteroarenes.
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Submitted on : Tuesday, April 9, 2019 - 1:47:45 PM
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Marie-Gabrielle Braun, Georgette Castanedo, Ling Qin, Patrick Salvo, Samir Zard. Introduction of Trifluoroethylamine as Amide Isostere by C–H Functionalization of Heteroarenes. Organic Letters, American Chemical Society, 2017, 19 (15), pp.4090-4093. ⟨10.1021/acs.orglett.7b01880⟩. ⟨hal-02094015⟩

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