398486-64-1Relevant academic research and scientific papers
Highly stereoselective synthesis of (E)- and (Z)-α-fluoro-α, β-unsaturated esters and (E)- and (Z)-α-fluoro-α,β- unsaturated amides from 1-bromo-1-fluoroalkenes via palladium-catalyzed carbonylation reactions
Xu, Jianjun,Burton, Donald J.
, p. 4346 - 4353 (2005)
The highly stereoselective synthesis of (E)- and (Z)-α-fluoro- α,β-unsaturated esters and (E)- and (Z)-α-fluoro-α, β-unsaturated amides is described. 1-Bromo-1-fluoroalkenes (E/Z ≈ 1:1), which are readily available starting materials, have been found to i
Kinetic separation methodology for the stereoselective synthesis of (E)- and (Z)-alpha-fluoro-alpha,beta-unsaturated esters via the palladium-catalyzed carboalkoxylation of 1-bromo-1-fluoroalkenes.
Xu, Jianjun,Burton, Donald J
, p. 831 - 833 (2007/10/03)
[reaction: see text] Methodology for the stereoselective preparation of both (E)- and (Z)-alpha-fluoro-alpha,beta-unsaturated esters is described. 1-Bromo-1-fluoroalkenes (E/Z approximate 1:1) can be isomerized to high E/Z ratio mixtures, which participat
A kinetic separation method for the stereoselective preparation of 1-fluorovinylphosphonates from E/Z mixtures of 1-bromo-1-fluoroolefins
Zhang,Burton
, p. 47 - 54 (2007/10/03)
Reaction of E/Z mixtures of 1-bromo-1-fluoroolefins with diethylphosphite and catalytic Pd(PPh3)4 in triethylamine at 30-40°C gave predominately the (E)-isomer of the 1-fluorovinylphosphonate (E/Z ≥ 95:5) in good yields. Pure (E)-1-f
A kinetic separation method for the stereoselective preparation of (Z)- and (E)-monofluoroenynes from E/Z mixtures of 1-bromo-1-fluoroolefins
Zhang, Xin,Burton, Donald J.
, p. 317 - 324 (2007/10/03)
Reaction of E/Z mixtures of 1-bromo-1-fluoroolefins with 1-alkynes and catalytic Pd(PPh3)2Cl2 and CuI in triethylamine at room temperature gave (after 16-24h) predominately the (Z)-monofluoroenyne (Z/E>92/8) in good yields. Pure (Z)-monofluoroenyne could generally be obtained by chromatographic separation of the crude Z/E mixture. Pure (Z)-1-bromo-1-fluoroolefin could he recovered and reacted with 1-alkynes under similar conditions and longer reaction times (48h) to give pure (E)-monofluoroenynes in excellent yields (78-89%). Thus, E/Z mixtures of 1-bromo-1-fluoroolefins could be kinetically separated into (Z)- and (E)-monofluoroenynes. This methodology provides a simple one-step unequivocal route to the isomerically pure (Z)- and (E)-monofluoroenynes from the readily available 1-bromo-1-fluoroolefins.
