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

Marie-Gabrielle Braun; Georgette Castanedo; Ling Qin; Patrick Salvo; Samir Zard

doi:10.1021/acs.orglett.7b01880

Journal articles

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

Marie-Gabrielle Braun ^{1, *} Georgette Castanedo ¹ Ling Qin ² Patrick Salvo ¹ Samir Zard ^{2, *}

* Corresponding author

1 Department of Discovery Chemistry

2 DCSO - Laboratoire de synthèse organique

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.

Document type :

Journal articles

Domain :

Chemical Sciences / Organic chemistry

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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, April 12, 2019 - 1:31:51 AM

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

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

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