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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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https://hal-polytechnique.archives-ouvertes.fr/hal-02094015
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Submitted on : Tuesday, April 9, 2019 - 1:47:45 PM
Last modification on : Friday, January 7, 2022 - 3:47:21 AM

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Marie-Gabrielle Braun, Georgette Castanedo, Ling Qin, Patrick Salvo, Samir Z. 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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