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Efficient Trifluoromethylation of Activated and Non‐Activated Alkenyl Halides by Using (Trifluoromethyl)trimethylsilane
Author(s) -
Hafner Andreas,
Bräse Stefan
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100528
Subject(s) - trifluoromethylation , chemistry , trifluoromethyl , halide , iodide , trimethylsilane , potassium fluoride , copper , solvent , chelation , fluoride , organic chemistry , inorganic chemistry , alkyl
An efficient method for the trifluoromethylation of halogenated double bonds by using in situ generated “trifluoromethyl copper” is described. Herein, the most common trifluoromethyl source, (trifluoromethyl)trimethylsilane, was converted selectively into “trifluoromethyl copper” by using copper iodide as copper source and potassium fluoride as promoter. In 1,3‐dimethyl‐3,4,5,6‐tetrahydro‐2(1 H )‐pyrimidinone (DMPU) as chelating solvent the trifluoromethylation of activated and non‐activated alkenyl halides occurred mostly in good to excellent yields in up to a gram scale.