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Synthesis and Use of Trifluoromethylthiolated Ketenimines
Author(s) -
Guérin Thomas,
Pikun Nadiia V.,
Morioka Ryutaro,
Panossian Armen,
Hanquet Gilles,
Leroux Frédéric R.
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202002723
Subject(s) - beckmann rearrangement , substituent , moiety , nucleophile , deprotonation , chemistry , combinatorial chemistry , computational chemistry , organic chemistry , ion , oxime , catalysis
The synthesis of trifluoromethylthiolated ketenimines is herein described. They are easily synthesized from the corresponding α‐trifluoromethylthiolated oximes upon activation with triflic anhydride and a base. The presumed nitrilium ion resulting from the Beckmann rearrangement is deprotonated to lead to the key intermediate, whose stability brought by the fluorinated substituent was unforeseeable. The reaction of these new building blocks with a variety of nucleophiles affords a vast array of cyclic and acyclic products bearing the valuable SCF 3 moiety.