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

Complete list of metadata

https://hal-polytechnique.archives-ouvertes.fr/hal-02094015
Contributor : Aurélien Arnoux Connect in order to contact the contributor
Submitted on : Tuesday, April 9, 2019 - 1:47:45 PM
Last modification on : Friday, January 7, 2022 - 3:47:21 AM

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

Licence

Identifiers

Collections

Citation

Export

Metrics

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

Licence

Identifiers

Collections

Citation

Export

Share

Metrics