1. Oxidative 3,3,3-trifluoropropylation of arylaldehydes
- Author
-
Akari Ikeda, Masaaki Omote, Shiho Nomura, Miyuu Tanaka, Atsushi Tarui, Kazuyuki Sato, and Akira Ando
- Subjects
cesium fluoride ,organo-fluorine ,1,3-proton shift ,trifluoromethyl ,3,3,3-trifluoropropenyl ,Science ,Organic chemistry ,QD241-441 - Abstract
A reaction between (E)-trimethyl(3,3,3-trifluoroprop-1-en-1-yl)silane (1) and arylaldehydes 2 was triggered by fluoride anions to afford aryl 3,3,3-trifluoropropyl ketones 3 in moderate to good yield. A mechanistic study of this reaction indicated that it occurred via an allyl alkoxide (4). A subsequent 1,3-proton shift of the benzylic proton of 4 forms 3. This reaction involves oxidative 3,3,3-trifluoropropylation of an arylaldehyde to afford 4,4,4-trifluoro-1-arylbutan-1-one.
- Published
- 2013
- Full Text
- View/download PDF