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Iron‐Catalyzed Decarboxylation of Trifluoroacetate and Its Application to the Synthesis of Trifluoromethyl Thioethers
Author(s) -
Exner Benjamin,
Bayarmagnai Bilguun,
Jia Fan,
Goossen Lukas J.
Publication year - 2015
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.201503915
Subject(s) - decarboxylation , trifluoromethylation , trifluoromethyl , chemistry , nucleophile , catalysis , potassium , chloride , organic chemistry , medicinal chemistry , combinatorial chemistry , alkyl
Nucleophilic CF 3 has been generated by decarboxylation of potassium trifluoroacetate, arguably the most easy‐to‐handle, inexpensive, and sustainable source of trifluoromethyl groups. Simple iron(II) chloride catalyzes the decarboxylation as well as a subsequent trifluoromethylation of organothiocyanates, resulting in a straightforward synthesis of trifluoromethyl thioethers. The KCN byproduct is absorbed by iron(II) with formation of nontoxic potassium hexacyanoferrate. An analogous trifluoromethylation of aldehydes with trifluoroacetate underlines the synthetic potential of such iron‐catalyzed decarboxylative trifluoromethylations.