13679-56-6Relevant academic research and scientific papers
Photooxidations of 2-(γ,ε-dihydroxyalkyl) furans in water: Synthesis of DE-bicycles of the pectenotoxins
Kouridaki, Antonia,Montagnon, Tamsyn,Tofi, Maria,Vassilikogiannakis, Georgios
, p. 2374 - 2377 (2012)
Photooxygenations of 2-(γ,ε-dihydroxyalkyl) furans in H 2O followed by in situ reduction and ketalization affords, in one synthetic operation, DE-bicyclic ketals of the pectenotoxins.
Catalytic activity of cycloaurated complexes in the addition of 2-methylfuran to methyl vinyl ketone
Kilpin, Kelly J.,Jarman, Bevan P.,Henderson, William,Nicholson, Brian K.
, p. 810 - 814 (2011)
Cycloaurated gold(III) complexes derived from cycloaurated iminophosphorane, triphenylphosphine sulfide or selenide, or pyridylsulfonamide ligands have been assessed for their catalytic activity in the addition of 2-methylfuran to methyl vinyl ketone. Addition of AgBF4 was generally needed for high activity, although those with coordinated atoms of high trans influence showed some activity in the absence of added Ag+. Copyright
Effect of water on chemo- and endo-selectivity in high pressure Diels-Alder furan reactions. Hydrophobic or polar effects?
Jenner, Gerard
, p. 1189 - 1192 (1994)
Diels-Alder furan additions are less sensitive to pressure in aqueous solution than in organic solvents. In some cases, water affects chemo- and stereoselectivity. The interpretation takes into account hydrophobic as well as polar effects induced by water.
Functional group dependence of the acid catalyzed ring opening of biomass derived furan rings: An experimental and theoretical study
Waidmann, Christopher R.,Pierpont, Aaron W.,Batista, Enrique R.,Gordon, John C.,Martin, Richard L.,Pete Silks,West, Ryan M.,Wu, Ruilian
, p. 106 - 115 (2013)
We describe studies of Bronsted acid catalyzed ring opening of substituted furans contained within biomass derived C8- and C9- molecules. Ring opening occurs homogeneously under relatively mild conditions of 80°C using catalytic hydrochloric acid. In the case of 4-(5-methyl-2-furyl) -2-butanone (1a), the reaction proceeds to a single product in up to 92% yield after 24 hours. For 4-(2-furanyl)-2-butanone (1b) and 4-(5-hydroxymethyl)-2- furanyl-2-butanone (1c), however, multiple products are observed, illustrating the significant influence of furan ring substituents on the reactivity of this class of compounds. The generality of these reaction pathways was tested using several other similar substrates. Kinetics experiments indicate that ring opening of 1a occurs via specific acid catalysis, and computations elucidate the effect of initial protonation on the reaction pathway. Calculated pK a values were calibrated against experimentally measured values and are consistent with observed reactivities. Inclusion of explicit, hydrogen-bonded water molecules in addition to the SMD solvent model is necessary when studying protonation of alcohol and ketone groups. The Royal Society of Chemistry 2013.
CHEMOSELECTIVE REDUCTION IN CARBONYL-CONJUGATED VINYLFURANS BY THE Mg/MeOH SYSTEM
Dominguez, Carmen,Csaky, Aurelio G.,Plumet, Joaquin
, p. 4183 - 4184 (1991)
Chemoselective reduction of double bonds conjugated with carbonyl groups and furan rings has been accomplished by using Mg/MeOH reducing system.
High-pressure effect on organic reactions in fluorophobic media
Jenner, Gerard,Gacem, Badra
, p. 265 - 270 (2003)
The kinetic effect of fluorophobic interactions was examined in Diels-Alder reactions and the conjugate addition of amines to acrylonitrile at different pressures. Its magnitude is lower than for other solvophobic media (water, ethylene glycol). Activatio
Michael Additions Catalyzed by a β-Diketiminate-Supported Aluminum Complex
Liu, Zhizhou,Vidovi?, Dragoslav
, p. 5295 - 5300 (2018)
A β-diketiminate-supported aluminum bistriflate complex (DipLAl(OTf)2·Na[BArCl4]; DipL = CH(CMe)2(N-C6H3-iPr2)2; Tf = O2SCF
Halogen Bond-Catalyzed Friedel?Crafts Reactions of Furans Using a 2,2’-Bipyridine-Based Catalyst
Zhang, Huimiao,Toy, Patrick H.
supporting information, p. 215 - 221 (2020/12/01)
A halogen bond donor based on a 2,2’-bipyridine framework has been synthesized, and used to catalyze Friedel?Crafts reactions of furans. Electrophiles used successfully in these reactions included various enones, an aldehyde, and a carboxylic acid anhydride. The yields of the reactions were generally good using a moderate catalyst loading (0.025 or 0.1 equiv.) at a relatively low temperature (room temp. or 50 °C) in acetonitrile. The catalyst used was designed with a biaryl scaffold so that if it indeed proved to be an efficient halogen bond donor organocatalyst, an enantioenriched version of it could potentially serve as a stereoselective catalyst. (Figure presented.).
Copper(II) bromide-catalyzed conjugate addition of furans to α,β-unsaturated carbonyl compounds
Fadeev, Alexander A.,Uchuskin, Maxim G.,Trushkov, Igor V.,Makarov, Anton S.
, p. 1286 - 1293 (2018/01/27)
[Figure not available: see fulltext.] A simple method for the synthesis of 2-(3-oxoalkyl)furan derivatives based on conjugate addition of 2-substituted furans to various α,β-unsaturated carbonyl compounds in the presence of copper(II) bromide as catalyst was developed.
B(C6F5)3-Catalyzed Michael Reactions: Aromatic C-H as Nucleophiles
Li, Wu,Werner, Thomas
supporting information, p. 2568 - 2571 (2017/05/24)
The Michael reaction is a widely used reaction for the C-C coupling of electron-poor olefins and C(sp3)-H pronucleophiles. Herein we report the Michael reaction between alkenes and aromatic as well as heteroaromatic compounds as aromatic C(sps
