22332-67-8Relevant academic research and scientific papers
Palladium-Catalyzed Stereoconvergent Formylation of (E/Z)-β-Bromo- β-fluorostyrenes: Straightforward Access to (Z)-α-Fluorocinnamic Aldehydes and (Z)-β-Fluorocinnamic Alcohols
Zemmouri, Rajae,Kajjout, Mohammed,Castanet, Yves,Eddarir, Said,Rolando, Christian
experimental part, p. 7691 - 7698 (2011/12/02)
We report here the stereoconvergent formylation of (E/Z)-β-bromo- β-fluorostyrene mixtures with carbon monoxide and sodium formate catalyzed by palladium. Optimization of reaction conditions leads to the corresponding pure (Z)-α-fluorocinnamaldehydes in g
Synthesis and Horner-Wittig Chemistry of (Fluoromethyl)diphenylphosphane Oxide
Steenis, Jan Hein van,Gen, Arne van der
, p. 897 - 910 (2007/10/03)
(Fluoromethyl)diphenylphosphane oxide (1) was obtained by heating (diphenylphosphinoyl)methyl p-toluenesulfinate (2) with potassium fluoride. Compound 1 is a stable, crystalline solid, suitable for application in the Horner-Wittig reaction. The compound described in the literature under this name was found to be benzylphenylphosphinic fluoride (5). The anion of phosphane oxide 1 readily reacted with a wide range of carbonyl to yield diastereomeric mixtures of α-fluoro-β-(hydroxyalkyl)phosphane oxides (7), which in most cases could be separated. The ease of phosphinate elimination to yield (E)- and (Z)-1-fluoroalkenes 8 stereoselectively was found to be strongly dependent upon conformation and substituent patern. The route presented here avoids the use of hazardous fluorohalomethanes, which were employed in several earlier Wittig-related approaches to vinyl fluorides.
