55591-26-9Relevant academic research and scientific papers
Allyl coupling reaction method and application thereof
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Paragraph 0070-0075, (2021/08/25)
The invention discloses a novel allyl coupling reaction method which takes an allyl thianthene salt as an allylation reagent and respectively takes a carboxylic acid compound. An allylated coupling product is obtained by reacting a substrate with a base in the presence of a base, or directly with a carboxylate compound, an aromatic hydrocarbon/heterocyclic hydrocarbon as a substrate, and at room temperature. The preparation method is mild in condition and free of transition metal participation, can efficiently realize preparation of various allyl ester, allyl substituted amine and allyl substituted aromatic hydrocarbon/heterocyclic hydrocarbon compound, and has an ideal application prospect in the fields of fine chemical engineering, material science and pharmacy.
Sol–Gel Immobilized N-Heterocyclic Carbene Gold Complex as a Recyclable Catalyst for the Rearrangement of Allylic Esters and the Cycloisomerization of γ-Alkynoic Acids
Ferré, Meritxell,Catto?n, Xavier,Wong Chi Man, Michel,Pleixats, Roser
, p. 2824 - 2831 (2016/09/13)
The synthesis of a bis-silylated (NHC)AuCl (NHC=N-heterocyclic carbene) complex and the formation of a hybrid silica material by the sol–gel process by cogelification with tetraethylorthosilicate under fluoride catalysis are described. This material was characterized by using 29Si solid-state NMR spectroscopy, N2 sorption measurements, electron microscopy, and elemental analysis. It was tested as a reusable catalyst in the rearrangement of allylic esters in conjunction with a silver salt under microwave conditions and it displayed a much better performance than a homogeneous analogue. This catalyst is active and recyclable in the cycloisomerization of γ-alkynoic acids to five-membered enol-lactones at room temperature in two reaction media, a toluene/water biphasic system and a deep eutectic solvent.
Spiroadamantyl 1,2,4-trioxolane, 1,2,4-trioxane, and 1,2,4-trioxepane pairs: Relationship between peroxide bond iron(II) reactivity, heme alkylation efficiency, and antimalarial activity
Wang, Xiaofang,Creek, Darren J.,Schiaffo, Charles E.,Dong, Yuxiang,Chollet, Jacques,Scheurer, Christian,Wittlin, Sergio,Charman, Susan A.,Dussault, Patrick H.,Wood, James K.,Vennerstrom, Jonathan L.
scheme or table, p. 4542 - 4545 (2010/06/15)
These data suggest that iron(II) reactivity for a set of homologous spiroadamantyl 1,2,4-trioxolane, 1,2,4-trioxane, and 1,2,4-trioxepane peroxide heterocycles is a necessary, but insufficient, property of animalarial peroxides. Heme alkylation efficiency appears to give a more accurate prediction of antimalarial activity than FeSO4-mediated reaction rates, suggesting that antimalarial activity is not merely dependent on peroxide bond cleavage, but also on the ability of reactive intermediates to alkylate heme or other proximal targets.
[(NHC)Au1]-catalyzed rearrangement of allylic acetates
Marion, Nicolas,Gealageas, Ronan,Nolan, Steven P.
, p. 2653 - 2656 (2008/02/09)
Equation Presented [(NHC)AuCl] complexes (NHC = N-heterocyclic carbene), in conjunction with a silver salt, were found to efficiently catalyze the rearrangement of allylic acetates under both conventional and microwave-assisted heating. The optimization of several reaction parameters (solvent, silver salt, and ligand) as well as a study of the reaction scope are reported. The steric hindrance of the ligand bound to gold was found crucial for the outcome of the reaction as only extremely bulky ligands permitted the isomerization.
Convenient and efficient Pd-catalyzed regioselective oxyfunctionalization of terminal olefins by using molecular oxygen as sole reoxidant
Mitsudome, Takato,Umetani, Takuya,Nosaka, Naoya,Mori, Kohsuke,Mizugaki, Tomoo,Ebitani, Kohki,Kaneda, Kiyotomi
, p. 481 - 485 (2007/10/03)
(Chemical Equation Presented) Just the one: The combination of palladium dichloride and N,N-dimethylacetamide (DMA) constitutes a highly efficient and reusable catalytic system, which uses molecular oxygen as the sole reoxidant for liquid-phase Wacker oxidation and acetoxylation of terminal olefins to the corresponding methyl ketones and linear allylic acetates, respectively (see scheme). 2006 Wiley-VCH Verlag GmbH Co. KGaA.
Regioselective Photocycloadditions of Benzoquinones to Alkylidenecyclohexanes: A New Synthetic Resource
Ciufolini, Marco A.,Rivera-Fortin, M. Angelica,Byrne, Norman E.
, p. 3505 - 3508 (2007/10/02)
Benzoquinones add regioselectively to alkylidenecyclohexanes.The photoadducts are converted into useful building blocks in good yield.
AN EFFICIENT SYNTHETIC ROUTE TO γ,δ-UNSATURATED SEVEN-MEMBERED LACTONES
Kido, Fusao,Kazi, Abul B.,Yamaji, Kazuo,Kato, Michiharu,Yoshikoshi, Akira
, p. 607 - 618 (2007/10/02)
Treatment of the diazomalonates (9a-d) of 2-phenylthio-3-butenol derivatives with catalytic rhodium acetate resulted in the sigmatropic rearrangement of six-membered allylsulfonium ylides to provide γ,δ-unsaturated seven-membered lactones (10a-d) in
Preparation of Allylic Acetates from Simple Alkenes by Palladium(II)-Catalyzed Acetoxylation
Hansson, Sverker,Heumann, Andreas,Rein, Tobias,Akermark, Bjoern
, p. 975 - 984 (2007/10/02)
The scope and limitations of palladium-catalyzed allylic acetoxylation has been investigated, using benzoquinone-manganese dioxide as the reoxidation system.Unsubstituted cycloalkenes gave good to excellent yields of allylic acetates.Total yields were also good for many substituted cycloalkenes and for linear alkenes, but these substrates generally gave several isomeric acetates.The exploratory mechanistic studies show that the acetoxylation can proceed via both 1,2-acetoxypalladation and η3-allylpalladium complex formation.The keen balance between these processes depends on the structure of the alkene.
New Entry to γ,δ-Unsaturated Seven-membered Lactones
Kido, Fusao,Kazi, Abul B.,Yoshikoshi, Akira
, p. 613 - 616 (2007/10/02)
The sigmatropic rearrangement of cyclic allyl-sulfonium ylides, generated from the diazo malonates of 2-phenylthio-3-butenol derivatives with catalytic rhodium acetate, afforded γ,δ-unsaturated seven-membered lactones in moderate to good yields.
