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Direct Synthesis of Thiocarbamoyl Fluorides and Trifluoromethylamines Through Fluorinative Desulfurization
Author(s) -
Onida Killian,
Vanoye Laurent,
Tlili Anis
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901113
Subject(s) - flue gas desulfurization , fluoride , carbon disulfide , sulfur , chemistry , trifluoride , disulfide bond , carbon fibers , organic chemistry , inorganic chemistry , combinatorial chemistry , materials science , biochemistry , composite number , composite material
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)sulfur trifluoride (DAST). The title compounds were obtained in moderate to very good isolated yields. Furthermore, we demonstrated also that thiocarbamoyl fluoride can be converted into their trifluoromethylamine analogues through simple treatment with silver fluoride.