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Direct Preparation of Trifluoromethyl Ketones from Carboxylic Esters: Trifluoromethylation with (Trifluoromethyl)trimethylsilane
Author(s) -
Wiedemann Jürgen,
Heiner Thomas,
Mloston Gregorz,
Prakash G. K. Surya,
Olah George A.
Publication year - 1998
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19980403)37:6<820::aid-anie820>3.0.co;2-m
Subject(s) - trifluoromethylation , trifluoromethyl , trimethylsilane , chemistry , carboxylic acid , organic chemistry , alkyl
Previously difficult to prepare , aliphatic and alicyclic trifluoromethylketones (e.g. 1 and 2 ), which are of pharmacalogic interest as potential enzyme inhibitors, can now be synthesized easily and efficiently. The one‐step reaction starting with carbonic esters and trimethyl(trifluoromethyl)silane is induced by tetrabutylammonium fluoride in nonpolar, aprotic solvents and proceeds without formation of double‐addition products.