75290-86-7Relevant academic research and scientific papers
Pillar[5]arene-Based 3D Hybrid Supramolecular Polymer for Green Catalysis in Water
Cai, Yan,Yan, Xin,Wang, Siyuan,Zhu, Zhiwen,Cen, Moupan,Ou, Changjin,Zhao, Qin,Yan, Qian,Wang, Jin,Yao, Yong
supporting information, p. 2883 - 2887 (2021/03/01)
Pillar[n]arene-based supramolecular polymers have attracted great interest because of their tunable morphologies and external stimuli responsiveness. However, most of the investigations of supramolecular polymers previously reported were focused on their formation and transformation, and investigations on their applications are rare. Herein, we designed and prepared hybrid polymeric materials by incorporating Pd nanoparticles into a supramolecular polymer, constructed from a pillar[5]arene dimer and a three-arm guest. The obtained hybrid polymer was fully characterized by scanning electron microscopy, transmission electron microscopy, X-ray photoelectron spectroscopy, scanning electron microscopy-energy-dispersive X-ray mapping, and X-ray diffraction technologies. Importantly, the hybrid supramolecular polymeric materials exhibited desirable catalytic activity for reductions of toxic nitroaromatics and C-C bond-forming Suzuki-Miyaura reaction in aqueous solution.
Enantioselective Heck Arylation of Acyclic Alkenol Aryl Ethers: Synthetic Applications and DFT Investigation of the Stereoselectivity
Polo, Ellen Christine,Wang, Martí Fernández,Angnes, Ricardo Almir,Braga, Ataualpa A. C.,Correia, Carlos Roque Duarte
supporting information, p. 884 - 892 (2019/12/30)
Herein we report the enantioselective Heck-Matsuda arylation of acyclic E and Z-alkenyl aryl ethers. The reactions were carried out under mild conditions affording the enantioenriched benzyl ethers in a regioselective manner, moderate to good yields (up to 73%), and in good to excellent enantiomeric ratios (up to 97:3). The enantioselective Heck-Matsuda arylation has shown a broad scope (25 examples), and some key Heck-Matsuda adducts were further converted into more complex and valuable scaffolds including their synthetic application in the synthesis of (R)-Fluoxetine, (R)-Atomoxetine, and in the synthesis of an enantioenriched benzo[c]chromene. Finally, in silico mechanistic investigations into the reaction's enantioselectivity were performed using density functional theory. (Figure presented.).
A Fluorescence Polarization Assay for Binding to Macrophage Migration Inhibitory Factor and Crystal Structures for Complexes of Two Potent Inhibitors
Cisneros, José A.,Robertson, Michael J.,Valhondo, Margarita,Jorgensen, William L.
supporting information, p. 8630 - 8638 (2016/07/27)
Human macrophage migration inhibitory factor (MIF) is both a keto-enol tautomerase and a cytokine associated with numerous inflammatory diseases and cancer. Consistent with observed correlations between inhibition of the enzymatic and biological activities, discovery of MIF inhibitors has focused on monitoring the tautomerase activity using l-dopachrome methyl ester or 4-hydroxyphenyl pyruvic acid as substrates. The accuracy of these assays is compromised by several issues including substrate instability, spectral interference, and short linear periods for product formation. In this work, we report the syntheses of fluorescently labeled MIF inhibitors and their use in the first fluorescence polarization-based assay to measure the direct binding of inhibitors to the active site. The assay allows the accurate and efficient identification of competitive, noncompetitive, and covalent inhibitors of MIF in a manner that can be scaled for high-throughput screening. The results for 22 compounds show that the most potent MIF inhibitors bind with Kd values of ca. 50 nM; two are from our laboratory, and the other is a compound from the patent literature. X-ray crystal structures for two of the most potent compounds bound to MIF are also reported here. Striking combinations of protein-ligand hydrogen bonding, aryl-aryl, and cation-π interactions are responsible for the high affinities. A new chemical series was then designed using this knowledge to yield two more strong MIF inhibitors/binders.
Metal-free oxidative cyclization of alkynyl aryl ethers to benzofuranones
Graf, Katharina,Ruehl, Carmen L.,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
supporting information, p. 12727 - 12731 (2013/12/04)
Readily available phenols can be converted into substituted aryl alkynyl ethers, which react with an N-oxide as an oxidant and catalytic amounts of a Bronsted acid to provide benzofuranones. If non-terminal alkynyl ethers are applied, a 1,2-hydride shift takes place and phenyl acrylates are obtained. Thus activated alkynes can serve as α-oxy carbene precursors even in the absence of a metal catalyst. Copyright
Fluorinated 5- and 7-membered carbacycle motifs by reaction of difluorocarbene with acetylene ethers
Chia, Poh Wai,Bello, Davide,Slawin, Alexandra M. Z.,O'Hagan, David
, p. 2189 - 2191 (2013/03/29)
The reaction of acetylene ethers with difluorocarbene (CF2), generated from the Ruppert-Prakash reagent, unexpectedly gave rise to co-produced fluorinated bicyclic [2.1.1]-hex-2-ene and cyclohepta-1,4-diene ring products.
Rhodium-catalyzed complete regioselective lntermolecular cross-cyclotrimerization of aryl ethynyl ethers and nitriles or isocyanates at room temperature
Komine, Yoshiyuki,Tanaka, Ken
supporting information; experimental part, p. 1312 - 1315 (2010/06/15)
Chemical Equation Presented We have established that a catlonic rhodium(I)/H8- BINAP complex catalyzes the complete regioselective intermolecular cross-cyclotrimerizatlon of aryl ethynyl ethers and nitriles or isocyanates leading to 2,4-diaryloxypyrldines or 4,6-diaryloxy-2-pyridones at room temperature.
Gold catalysis: Switching the pathway of the furan-yne cyclization
Hashmi, A. Stephen K.,Rudolph, Matthias,Huck, Juergen,Frey, Wolfgang,Bats, Jan W.,Hamzic, Melissa
supporting information; experimental part, p. 5848 - 5852 (2009/12/06)
Changing tracks: By the use of alkynyl ethers as directing elements, the furan-yne cyclization enters a new reaction pathway. Instead of phenols, tetracycles containing two heteroatoms and two new stereocenters are formed (see scheme).
