729613-11-0Relevant academic research and scientific papers
A facile and mild method for the synthesis of terminal bromofluoroolefins via diethylzinc-promoted wittig reaction
Lei, Xinsheng,Dutheuil, Guillaume,Pannecoucke, Xavier,Quirion, Jean-Charles
, p. 2101 - 2104 (2004)
Synthesis of 1-bromo-1-fluoroolefins was achieved in good yields via a Wittig reaction promoted by diethylzinc, even with nonactivated aldehydes and ketones as starting materials.
Reactions of carbonyl compounds with phosphorus ylide generated from tribromofluoromethane and tris(dimethylamino)phosphine
Hirai, Go,Nishizawa, Eri,Kakumoto, Daiki,Morita, Masaki,Okada, Mitsuaki,Hashizume, Daisuke,Nagashima, Sayoko,Sodeoka, Mikiko
supporting information, p. 1389 - 1391 (2015/11/17)
The reactions of fluorinated ylide, generated from tris(dimethylamino) phosphine and tribromofluoromethane, with simple aldehydes and reactive ketones gave the expected Wittig reaction products. However, a ketone having a galactose skeleton afforded an acid fluoride, probably through an unprecedented CoreyChaykovski- type epoxide formation reaction, followed by spontaneous Meinwald rearrangement.
Efficient synthesis of fluoroalkenes via diethylzinc-promoted wittig reaction
Zoute, Ludivine,Dutheuil, Guillaume,Quirion, Jean-Charles,Jubault, Philippe,Pannecoucke, Xavier
, p. 3409 - 3418 (2008/02/11)
The synthesis of α-fluoroacrylates and α-bromo-α- fluoroalkenes was achieved in very good yields using aldehydes and ketones, triphenylphosphine, diethylzinc as promoter, and ethyl dibromofluoroacetate or dibromofluoromethane, respectively. A change in th
Stereoselective synthesis of 1-bromo-1-fluorostyrenes
Shastin, Aleksey V.,Muzalevsky, Vasiliy M.,Balenkova, Elizabeth S.,Nenajdenko, Valentine G.
, p. 179 - 180 (2007/10/03)
The effective and stereoselective one-pot synthesis of 1-bromo-1- fluorostyrenes from aromatic aldehydes based on a catalytic olefination reaction was elaborated.
First stereospecific synthesis of (E)- or (Z)-α-fluoroenones via a kinetically controlled Negishi coupling reaction
Dutheuil, Guillaume,Paturel, Clotilde,Lei, Xinsheng,Couve-Bonnaire, Samuel,Pannecoucke, Xavier
, p. 4316 - 4319 (2007/10/03)
A highly stereospecific synthesis of (E)- or (Z)-α-fluoro-α, β-unsaturated ketones 4, via a kinetically controlled Negishi palladium-catalyzed coupling reaction, was developed, providing an easy and general access to valuable fluorinated intermediates (pharmaceutical, peptide mimic, and so on). The synthesis involved a reaction between E/Z gem-bromofluoroolefins 2 and alkoxyvinylzinc species 6 under controlled reaction temperature. At 10 °C, (Z)-4 (70 to 99% yields) was obtained along with unreacted (Z)-2 (66 to 99% yields). At THF reflux, the recovered olefin was transformed into (E)-4 (up to 98% yield).
