5 years ago

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

Introduction of Trifluoroethylamine as Amide Isostere by C–H Functionalization of Heteroarenes
Marie-Gabrielle Braun, Samir Z. Zard, Ling Qin, Georgette Castanedo, Patrick Salvo
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01880

DOI: 10.1021/acs.orglett.7b01880

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