Direct Synthesis of Thiocarbamoyl Fluorides and Trifluoromethylamines Through Fluorinative Desulfurization

Killian Onida (1) , Laurent Vanoye (2) , Anis Tlili (1)

1 ICBMS - Institut de Chimie et Biochimie Moléculaires et Supramoléculaires
2 LGPC - Laboratoire de Génie des Procédés Catalytiques

Herein, a straightforward synthesis of thiocarbamoyl fluorides is reported starting from amines and carbon disulfide. The key to success is the fluorinative desulfurization of carbon disulfide with (diethylamino)sulfurtrifluroide (DAST). The title compounds were obtained in moderate to very good isolated yields. Furthermore, we demonstrated also that thiocarbamoyl fluoride can be converted to their trifluoromethyl amine analogues through simple treatment with silver fluoride.

Domaines: Chimie

Killian Onida, Laurent Vanoye, Anis Tlili. Direct Synthesis of Thiocarbamoyl Fluorides and Trifluoromethylamines Through Fluorinative Desulfurization. European Journal of Organic Chemistry, 2019, 2019 (35), pp.6106-6109. ⟨10.1002/ejoc.201901113⟩. ⟨hal-03008845⟩