Facile synthesis of fluoroalkenes by palladium-catalyzed reductive defluorination of allylic gem-difluorides.
Chemo- and stereoselective synthesis of fluoroalkenes was achieved in excellent yields via Pd-catalyzed C-F bond activation. In this transformation, Et3N plays a crucial role to produce reactive hydride species such as Ph(EtO)SiH2 and Ph(EtO)2SiH by promoting dehydrogenative coupling. The reaction proceeds efficiently at 50 degrees C with a variety of substrates and is also useful for the synthesis of fluoroalkene peptidomimetics.
Narumi
Tetsuo
T
Graduate School of Pharmaceutical Sciences, Kyoto University, Kyoto 606-8501, Japan.
Tomita
Kenji
K
Inokuchi
Eriko
E
Kobayashi
Kazuya
K
Oishi
Shinya
S
Ohno
Hiroaki
H
Fujii
Nobutaka
N
D000475:Alkenes / Q000138:chemical synthesis*; D002384:Catalysis; D005459:Fluorides / Q000737:chemistry; D006846:Hydrocarbons, Halogenated / Q000138:chemical synthesis*; D018716:Molecular Mimicry; D010165:Palladium / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis*
D000475:Alkenes; D006846:Hydrocarbons, Halogenated; D010455:Peptides; D010165:Palladium; D005459:Fluorides